The Experts below are selected from a list of 279 Experts worldwide ranked by ideXlab platform
Scott D. Rychnovsky - One of the best experts on this subject based on the ideXlab platform.
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Reductive spiroannulation of nitriles with secondary electrophiles.
Organic letters, 2005Co-Authors: Matthew D. Morin, Scott D. RychnovskyAbstract:The scope of reductive Decyanation and spiroannulation reactions has been expanded to include secondary electrophiles for potentially useful transformations. Secondary phosphates and chlorides, as well as terminal epoxides, cyclize in a stereospecific fashion. Both endo and exo modes of cyclization were observed with terminal epoxides.
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Synthesis of the Spirofungin B Core by a Reductive Cyclization Strategy
Organic letters, 2005Co-Authors: Thomas E. La Cruz, Scott D. RychnovskyAbstract:A reductive Decyanation approach to the synthesis of the core of spirofungin B has been developed. Spirofungin B has only one anomeric stabilization in the spiroacetal and was isolated along with its spiroacetal epimer, spirofungin A. The cyclization precursor was constructed from readily available starting materials. The reductive cyclization reaction was both efficient and stereoselective. The reductive cyclization strategy to spiroacetals is convergent and effective.
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Alkylation and Reductive Decyanation of 4-Cyano-2,2-dimethyl-1,3-dioxanes (Cyanohydrin Acetonides)
The Journal of Organic Chemistry, 1997Co-Authors: Scott D. Rychnovsky, Sonja S. SwensonAbstract:Cyanohydrin acetonide couplings are a very effective methodology for the synthesis of polyol chains. We report a detailed investigation of the alkylation and reductive Decyanation of 4-cyano-2,2-di...
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Tandem radical nitrile transfer-cyclization reactions of 1,3-dioxane-4-nitriles: Synthesis of spirocyclic systems
Tetrahedron, 1997Co-Authors: Scott D. Rychnovsky, Sonja S. SwensonAbstract:Abstract Reduction of remote halogen substituents with n-Bu3SnH leads to efficient 1,4- and 1,5-nitrile transfer from 1,3-dioxane-4-nitriles and subsequent stereoselective reduction. These radical-transfer reactions provide a mild alternative to the Li/NH3 reductive Decyanation previously used to generate syn-1,3-diols from 1,3-dioxane-4-nitriles. Compounds containing appropriate unsaturation undergo subsequent radical cyclization reactions to give spirocyclic products.
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Oxepanes from an unusual acetal cleavage of 6,8-dioxabicyclo[3.2.1]octanes
Tetrahedron Letters, 1996Co-Authors: Scott D. Rychnovsky, Vilas H. DahanukarAbstract:On treatment with BF3·OEt2 and TMSCN, epoxy ketone 1 cyclized to the bicyclic acetal 2, which then cleaved to give primarily the oxepane 5 as a single stereoisomer. Reductive Decyanation of 5 led to the oxepane 7, a structural unit present in the brevetoxin family of natural products. The scope and limitations of this reaction sequence were investigated.
Akio Kamimura - One of the best experts on this subject based on the ideXlab platform.
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HydroDecyanation of Secondary Alkyl Nitriles and Malononitriles to Alkanes using DiMeImd-BH3
The Journal of organic chemistry, 2020Co-Authors: Takuji Kawamoto, Kyohei Oritani, Atsushi Kawabata, Tsubasa Morioka, Hiroshi Matsubara, Akio KamimuraAbstract:The Decyanation of secondary aliphatic nitriles and the 2-fold Decyanation of malononitriles leading to alkanes in the presence of 1,3-dimethylimidazol-2-ylidene borane (diMeImd-BH3) are reported. ...
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Tris(trimethylsilyl)silane-Mediated Reductive Decyanation and Cyano Transfer Reactions of Malononitriles
Chemistry Letters, 2018Co-Authors: Takuji Kawamoto, Dennis P. Curran, Yudai Shimaya, Akio KamimuraAbstract:Reductive Decyanation reactions of malononitriles were achieved with tris(trimethylsilyl)silane as a radical mediator. The reaction proceeds via a radical chain mechanism involving a silyl radical addition to the malononitrile to form an imidoyl radical followed by α-cleavage to give a silyl isocyanide and an α-cyano radical. The reaction of a 3-butenyl-substituted malononitrile afforded a decyano/cyanosilylation product in good yield through 1,4-cyano transfer.
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Thiol-Catalyzed Radical Decyanation of Aliphatic Nitriles with Sodium Borohydride.
Organic letters, 2018Co-Authors: Takuji Kawamoto, Kyohei Oritani, Dennis P. Curran, Akio KamimuraAbstract:Radical Decyanation of aliphatic nitriles was achieved in the presence of NaBH4 and a thiol. The reaction proceeds via a radical mechanism involving borane radical anion addition to nitrile to form an iminyl radical, which undergoes carbon–carbon cleavage. Reductive radical addition to acrylonitrile is followed by Decyanation to give a two-carbon homologated product in a net radical ethylation reaction.
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Thiol-Catalyzed Radical Decyanation of Aliphatic Nitriles with Sodium Borohydride
2018Co-Authors: Takuji Kawamoto, Kyohei Oritani, Dennis P. Curran, Akio KamimuraAbstract:Radical Decyanation of aliphatic nitriles was achieved in the presence of NaBH4 and a thiol. The reaction proceeds via a radical mechanism involving borane radical anion addition to nitrile to form an iminyl radical, which undergoes carbon–carbon cleavage. Reductive radical addition to acrylonitrile is followed by Decyanation to give a two-carbon homologated product in a net radical ethylation reaction
Zhengwang Chen - One of the best experts on this subject based on the ideXlab platform.
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Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction.
The Journal of organic chemistry, 2020Co-Authors: Zhengwang Chen, Xiaowei Wen, Weiping Zheng, Dou Chen, Dingsheng Cao, Lipeng LongAbstract:Cu-catalyzed domino Decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C–CN cleavage yielding the correspo...
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A facile tandem Decyanation/cyanation reaction of α-iminonitriles toward cyano-substituted amides.
Organic & biomolecular chemistry, 2018Co-Authors: Zhengwang Chen, Pei Liang, Botao Liu, Haiqing Luo, Jing Zheng, Xiaowei Wen, Tanggao LiuAbstract:A new tandem Decyanation/cyanation reaction of α-iminonitriles has been developed. A variety of cyano-substituted aryl amides and heteroaryl amides are synthesized in good yields. Both electron-rich and electron-deficient groups are compatible with the standard conditions. This reaction features a nonmetallic cyano source, tandem Decyanation and cyanation reaction, waste utilization of the HCN from the hydrolysis of α-iminonitriles, formation of two important functional groups in one-step operation, etc.
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a facile tandem Decyanation cyanation reaction of α iminonitriles toward cyano substituted amides
Organic and Biomolecular Chemistry, 2018Co-Authors: Zhengwang Chen, Pei Liang, Botao Liu, Haiqing Luo, Jing Zheng, Xiaowei Wen, Tanggao LiuAbstract:A new tandem Decyanation/cyanation reaction of α-iminonitriles has been developed. A variety of cyano-substituted aryl amides and heteroaryl amides are synthesized in good yields. Both electron-rich and electron-deficient groups are compatible with the standard conditions. This reaction features a nonmetallic cyano source, tandem Decyanation and cyanation reaction, waste utilization of the HCN from the hydrolysis of α-iminonitriles, formation of two important functional groups in one-step operation, etc.
Tanggao Liu - One of the best experts on this subject based on the ideXlab platform.
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A facile tandem Decyanation/cyanation reaction of α-iminonitriles toward cyano-substituted amides.
Organic & biomolecular chemistry, 2018Co-Authors: Zhengwang Chen, Pei Liang, Botao Liu, Haiqing Luo, Jing Zheng, Xiaowei Wen, Tanggao LiuAbstract:A new tandem Decyanation/cyanation reaction of α-iminonitriles has been developed. A variety of cyano-substituted aryl amides and heteroaryl amides are synthesized in good yields. Both electron-rich and electron-deficient groups are compatible with the standard conditions. This reaction features a nonmetallic cyano source, tandem Decyanation and cyanation reaction, waste utilization of the HCN from the hydrolysis of α-iminonitriles, formation of two important functional groups in one-step operation, etc.
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a facile tandem Decyanation cyanation reaction of α iminonitriles toward cyano substituted amides
Organic and Biomolecular Chemistry, 2018Co-Authors: Zhengwang Chen, Pei Liang, Botao Liu, Haiqing Luo, Jing Zheng, Xiaowei Wen, Tanggao LiuAbstract:A new tandem Decyanation/cyanation reaction of α-iminonitriles has been developed. A variety of cyano-substituted aryl amides and heteroaryl amides are synthesized in good yields. Both electron-rich and electron-deficient groups are compatible with the standard conditions. This reaction features a nonmetallic cyano source, tandem Decyanation and cyanation reaction, waste utilization of the HCN from the hydrolysis of α-iminonitriles, formation of two important functional groups in one-step operation, etc.
Shusheng Zhang - One of the best experts on this subject based on the ideXlab platform.
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transformation of gem dicyanoethenes by samarium direct formation of indenes or direct Decyanation with in situ disilylation
European Journal of Organic Chemistry, 2008Co-Authors: Yongjun Liu, Fuqiang Zhang, Yongmin Zhang, Shusheng ZhangAbstract:Intramolecular cyclization of 1,1-diaryl-2,2-dicyanoethenes promoted by samarium metal in DMF in the presence of TMSCl allowed direct construction of the indene core, whereas 1-alkyl-1-aryl-2,2-dicyanoethenes underwent intermolecular coupling cyclization and Decyanation under the same conditions. Simultaneously, disilylation occurred at the amino moiety resulting from the reduction of the cyano group. However, only simple reduction of the C=C bonds is observed when a trace amount of water presented.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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Transformation of gem‐Dicyanoethenes by Samarium: Direct Formation of Indenes or Direct Decyanation with in Situ Disilylation
European Journal of Organic Chemistry, 2008Co-Authors: Yongjun Liu, Fuqiang Zhang, Yongmin Zhang, Shusheng ZhangAbstract:Intramolecular cyclization of 1,1-diaryl-2,2-dicyanoethenes promoted by samarium metal in DMF in the presence of TMSCl allowed direct construction of the indene core, whereas 1-alkyl-1-aryl-2,2-dicyanoethenes underwent intermolecular coupling cyclization and Decyanation under the same conditions. Simultaneously, disilylation occurred at the amino moiety resulting from the reduction of the cyano group. However, only simple reduction of the C=C bonds is observed when a trace amount of water presented.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)