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A. K. Basak - One of the best experts on this subject based on the ideXlab platform.
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boron trifluoride diethyl etherate complex mediated allylation of baylis hillman adducts a facile synthesis of 1 5 dienes
Synthesis, 2008Co-Authors: Jhillu S. Yadav, Basi Subba V Reddy, Satadru S Mandal, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth allylic nucleophilic substitution (S N 2′) with Allyltrimethylsilane in the presence of BF 3 ·OEt 2 under mild reaction conditions to afford 1,5-diene derivatives in good yields with high selectivity.
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One-Pot Oxidative Allylation of Morita-Baylis-Hillman Adducts with Allyltrimethylsilane Promoted by Dess-Martin Periodinane/Boron Trifluoride-Diethyl Ether Complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with Allyltrimethylsilane in the presence of Dess-Martin periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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one pot oxidative allylation of morita baylis hillman adducts with Allyltrimethylsilane promoted by dess martin periodinane boron trifluoride diethyl ether complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B Subba V Reddy, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with Allyltrimethylsilane in the presence of Dess-Martin periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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IBX/Sc(OTf)3-promoted one-pot oxidative conjugate addition of Allyltrimethylsilane to Baylis–Hillman adducts
Tetrahedron Letters, 2007Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B. V. Subba Reddy, A. K. Basak, Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Baylis–Hillman adducts undergo smooth one-pot oxidative Michael addition with Allyltrimethylsilane in the presence of 2-iodoxybenzoic acid (IBX)/Sc(OTf)3 under mild conditions to afford homoallyl β-ketoesters in good yields with high 1,4-selectivity.
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ibx sc otf 3 promoted one pot oxidative conjugate addition of Allyltrimethylsilane to baylis hillman adducts
Tetrahedron Letters, 2007Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B Subba V Reddy, A. K. BasakAbstract:Baylis–Hillman adducts undergo smooth one-pot oxidative Michael addition with Allyltrimethylsilane in the presence of 2-iodoxybenzoic acid (IBX)/Sc(OTf)3 under mild conditions to afford homoallyl β-ketoesters in good yields with high 1,4-selectivity.
Jhillu S. Yadav - One of the best experts on this subject based on the ideXlab platform.
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Highly diastereoselective allylation of lactols and their ethers using molecular iodine
Tetrahedron Letters, 2009Co-Authors: Jhillu S. Yadav, B. V. Subba Reddy, A. Srinivas Reddy, Ch. Suresh Reddy, S. Satyanarayana RajuAbstract:Abstract Lactols and their ethers undergo smooth allylation with Allyltrimethylsilane in the presence of 5 mol % iodine in dichloromethane at −78 °C to afford C-allylfuranosides in good yields and with high diastereoselectivity. The use of iodine makes this method simple, convenient and practical. This is the first report on the allylation of lactols with Allyltrimethylsilane using molecular iodine as a catalyst. Enhanced diastereoselectivity is the key feature of this protocol.
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boron trifluoride diethyl etherate complex mediated allylation of baylis hillman adducts a facile synthesis of 1 5 dienes
Synthesis, 2008Co-Authors: Jhillu S. Yadav, Basi Subba V Reddy, Satadru S Mandal, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth allylic nucleophilic substitution (S N 2′) with Allyltrimethylsilane in the presence of BF 3 ·OEt 2 under mild reaction conditions to afford 1,5-diene derivatives in good yields with high selectivity.
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One-Pot Oxidative Allylation of Morita-Baylis-Hillman Adducts with Allyltrimethylsilane Promoted by Dess-Martin Periodinane/Boron Trifluoride-Diethyl Ether Complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with Allyltrimethylsilane in the presence of Dess-Martin periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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one pot oxidative allylation of morita baylis hillman adducts with Allyltrimethylsilane promoted by dess martin periodinane boron trifluoride diethyl ether complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B Subba V Reddy, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with Allyltrimethylsilane in the presence of Dess-Martin periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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IBX/Sc(OTf)3-promoted one-pot oxidative conjugate addition of Allyltrimethylsilane to Baylis–Hillman adducts
Tetrahedron Letters, 2007Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B. V. Subba Reddy, A. K. Basak, Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Baylis–Hillman adducts undergo smooth one-pot oxidative Michael addition with Allyltrimethylsilane in the presence of 2-iodoxybenzoic acid (IBX)/Sc(OTf)3 under mild conditions to afford homoallyl β-ketoesters in good yields with high 1,4-selectivity.
Yutaka Nishiyama - One of the best experts on this subject based on the ideXlab platform.
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Rhenium complex-catalyzed carbon-carbon formation of alcohols and organosilicon compounds
Tetrahedron Letters, 2018Co-Authors: Rui Umeda, Toshifumi Jikyo, Kazuki Toda, Issey Osaka, Yutaka NishiyamaAbstract:Abstract The coupling reactions of allylic and benzylic alcohols and Allyltrimethylsilane are efficiently catalyzed by a rhenium complex to give the corresponding 1,5-dienes and alkenes in moderate to good yields. Similarly, alcohols were coupled with ketene silyl acetals to form the corresponding esters.
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rhenium complex catalyzed allylation of acetals with Allyltrimethylsilane
Tetrahedron Letters, 2008Co-Authors: Yutaka Nishiyama, Keiko Shimoura, Noboru SonodaAbstract:Abstract It was confirmed that the treatment of acetals with Allyltrimethylsilane in the presence of a catalytic amount of the rhenium complex, ReBr(CO) 5 , gave the corresponding homoallylic ethers in excellent to good yields.
Chinpiao Chen - One of the best experts on this subject based on the ideXlab platform.
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hclo4 supported on silica gel a mild and efficient catalyst for hosomi sakurai reaction
Tetrahedron Letters, 2011Co-Authors: Kaliyappan Murugan, Chinpiao ChenAbstract:Abstract Perchloric acid supported on silica gel was found to be an efficient catalyst (2 mol %) for the Hosomi–Sakurai allylation of numerous aldehydes with Allyltrimethylsilane in the presence of benzyl alcohol. This method was also effective for the allylation of secondary alcohols under mild experimental conditions.
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HClO4-supported on silica gel: a mild and efficient catalyst for Hosomi–Sakurai reaction
Tetrahedron Letters, 2011Co-Authors: Kaliyappan Murugan, Chinpiao ChenAbstract:Abstract Perchloric acid supported on silica gel was found to be an efficient catalyst (2 mol %) for the Hosomi–Sakurai allylation of numerous aldehydes with Allyltrimethylsilane in the presence of benzyl alcohol. This method was also effective for the allylation of secondary alcohols under mild experimental conditions.
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Silicomolybdic Acid Supported on Silica Gel: An Efficient Catalyst for Hosomi—Sakurai Reactions.
ChemInform, 2011Co-Authors: Kaliyappan Murugan, Sankareswaran Srimurugan, Chinpiao ChenAbstract:The heteropolyacid efficiently catalyzes reactions of carbonyl compounds with Allyltrimethylsilane (II) in the presence of benzyl alcohol.
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Silicomolybdic acid supported on silica gel: an efficient catalyst for Hosomi–Sakurai reactions
Tetrahedron, 2011Co-Authors: Kaliyappan Murugan, Sankareswaran Srimurugan, Chinpiao ChenAbstract:Silicomolybdic acid that is supported on silica gel (50 wt %) efficiently catalyzes the high-yielding Hosomi–Sakurai allylation of carbonyl compounds by Allyltrimethylsilane in the presence of benzyl alcohol. The reaction rates of inactive substrates and the yields were greatly increased when preformed acetals were used as substrates.
Janusz Jurczak - One of the best experts on this subject based on the ideXlab platform.
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The stereochemical course of addition of Allyltrimethylsilane to protected l-alaninals and l-serinals in the presence of Lewis acids. Total synthesis of cis-(2R,3S)-3-hydroxyproline
Tetrahedron: Asymmetry, 2002Co-Authors: Daniel T. Gryko, P. Prokopowicz, Janusz JurczakAbstract:Abstract The influence of Lewis acids on the diastereoselectivity of the addition of Allyltrimethylsilane to a variety of protected l -alaninals and l -serinals was investigated and high levels of asymmetric induction were achieved. Stereochemical models for rationalisation of the results obtained are proposed. cis -(2 R ,3 S )-3-Hydroxyproline was synthesised starting from N -Cbz, O -TBS- l -serinal, in which the crucial step involves addition of Allyltrimethylsilane to the aldehyde in the presence of SnCl 4 .
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Asymmetric addition of Allyltrimethylsilane to N-tosylimine of (1R)-8-phenylmenthyl glyoxylate.
Chirality, 2001Co-Authors: Anna Kulesza, Janusz JurczakAbstract:The addition of Allyltrimethylsilane to chiral N-tosylimine derived from (1R)-8-phenylmenthyl glyoxylate is discussed. Various Lewis acids were applied in order to postulate the stereochemical model for this type of nucleophilic addition. Chirality 13:634–635, 2001. © 2001 Wiley-Liss, Inc.
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diastereoselective addition of Allyltrimethylsilane to n glyoxyloyl 2r bornane 10 2 sultam a new synthesis of s 1 2 pentanediol
Synthetic Communications, 1999Co-Authors: Katarzyna Kiegiel, Piotr Prokopowicz, Janusz JurczakAbstract:Abstract Addition of Allyltrimethylsilane (3) to N-glyoxyloyl-(2R)-bomane:0,2-sultam (4) in the presence of Lewis acid afforded, in high diastereoselecti vity, adduct (2'S)-6 which, after recrystallization, was hydrogenated to give optically pure (S)-1,2-pentanediol (1).
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diastereoselective addition of allylic reagents to chiral α ketoimides derived from oppolzer s sultam
Tetrahedron Letters, 1999Co-Authors: Katarzyna Kiegiel, Janusz JurczakAbstract:Abstract Additions of allylmagnesium chloride and allyl bromide in the presence of zinc dust to N -methyl- and N -phenylglyoxyloyl-(2 R )-bornane-10,2-sultam and the Lewis acid-mediated additions of Allyltrimethylsilane to these chiral α-ketoimides were studied. High diastereoselection in these reactions was observed, and in the case of the Allyltrimethylsilane/TiCl 4 additions, a change of direction of asymmetric induction was found.
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DIASTEREOSELECTIVITY CONTROL IN THE TICL4-MEDIATED ADDITION REACTION OF Allyltrimethylsilane TO N, O-PROTECTED (L)-SERINALS
Tetrahedron Letters, 1998Co-Authors: Janusz Jurczak, Piotr ProkopowiczAbstract:Abstract The TiCl 4 - and SnCl 4 -mediated addition reactions of Allyltrimethylsilane ( 1 ) to protected ( l )-serinals ( 2–5 ) were studied, and in the case of TiCl 4 a large influence of the N- and O-protecting groups on the stereochemical course was observed.