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Mark Lautens - One of the best experts on this subject based on the ideXlab platform.

  • Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes
    2016
    Co-Authors: Jennifer Tsoung, Adam Zajdlik, Katja Krämer, Clemence Liébert, Mark Lautens
    Abstract:

    An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and Intramolecular Friedel–Crafts Alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity

  • Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes
    The Journal of organic chemistry, 2011
    Co-Authors: Jennifer Tsoung, Katja Krämer, Adam Zajdlik, Clémence Liébert, Mark Lautens
    Abstract:

    An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and Intramolecular Friedel–Crafts Alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.

  • Diastereoselective Intramolecular Friedel—Crafts Alkylation of Tetralins.
    ChemInform, 2011
    Co-Authors: Clémence Liébert, Marion Kristina Brinks, Andrew G. Capacci, Matthew J. Fleming, Mark Lautens
    Abstract:

    A wide range of cis-hexahydrobenzophenanthridine-derived cyclic compounds is prepared in a mild reaction from the corresponding chiral tetralin substrates with retention of optical purity.

  • Diastereoselective Intramolecular Friedel–Crafts Alkylation of Tetralins
    Organic letters, 2011
    Co-Authors: Clémence Liébert, Marion Kristina Brinks, Andrew G. Capacci, Matthew J. Fleming, Mark Lautens
    Abstract:

    An efficient and versatile synthesis of cis-hexahydrobenzophenanthridines starting from readily available tetralins has been developed using an Intramolecular Friedel–Crafts Alkylation as a key step. The substrates were prepared via a highly stereocontrolled rhodium-catalyzed ring-opening reaction of meso-oxabicyclic alkenes and a hydrogenation sequence. Thus, a wide variety of complex tetracyclic compounds have been isolated with a high level of regio-, diastereo-, and enantioselectivity.

  • Diastereoselective Intramolecular Friedel–Crafts Alkylation of Tetralins
    Organic letters, 2011
    Co-Authors: Clémence Liébert, Marion Kristina Brinks, Andrew G. Capacci, Matthew J. Fleming, Mark Lautens
    Abstract:

    An efficient and versatile synthesis of cis-hexahydrobenzophenanthridines starting from readily available tetralins has been developed using an Intramolecular Friedel–Crafts Alkylation as a key ste...

Lin Dong - One of the best experts on this subject based on the ideXlab platform.

Masami Kamigaito - One of the best experts on this subject based on the ideXlab platform.

Meike Niggemann - One of the best experts on this subject based on the ideXlab platform.

  • Diastereoselective Synthesis of Indanes and Tetralins via Intramolecular Friedel–Crafts Reaction
    2016
    Co-Authors: Jeannemarie Begouin, Francesca Capitta, Meike Niggemann
    Abstract:

    An easy access to tetralin and indane skeletons has been developed using a diastereoselective Intramolecular Friedel–Crafts Alkylation. Treatment of diastereomeric mixtures of benzyl carbinols with a catalytic amount of Ca(NTf2)2/Bu4NPF6 yields the respective tetralin or indane in good yields with high levels of regio- and diastereoselectivity

  • calcium catalyzed synthesis of 1 2 disubstituted 3 benzazepines
    European Journal of Organic Chemistry, 2015
    Co-Authors: Helena Damsen, Meike Niggemann
    Abstract:

    A short and highly stereoselective chiral pool synthesis of tetrahydro-3-benzazepines as potential drug molecules is described, using simple enantiopure amino acids as the chiral building blocks. Intramolecular Friedel–Crafts Alkylation towards seven-membered rings was achieved with high diastereoselectivity for the first time and accomplished by a biocompatible calcium catalyst. The simple and cost efficient approach allows for the variation of all substituents in the 3-benzazepine by a change of the substitution pattern in one or more of the reagents, while leaving the general synthetic route unchanged. Furthermore, assignment of the absolute configuration of the 3-benzazepine derivative is straightforward, based on the amino acid building block employed.

  • Calcium‐Catalyzed Synthesis of 1,2‐Disubstituted 3‐Benzazepines
    European Journal of Organic Chemistry, 2015
    Co-Authors: Helena Damsen, Meike Niggemann
    Abstract:

    A short and highly stereoselective chiral pool synthesis of tetrahydro-3-benzazepines as potential drug molecules is described, using simple enantiopure amino acids as the chiral building blocks. Intramolecular Friedel–Crafts Alkylation towards seven-membered rings was achieved with high diastereoselectivity for the first time and accomplished by a biocompatible calcium catalyst. The simple and cost efficient approach allows for the variation of all substituents in the 3-benzazepine by a change of the substitution pattern in one or more of the reagents, while leaving the general synthetic route unchanged. Furthermore, assignment of the absolute configuration of the 3-benzazepine derivative is straightforward, based on the amino acid building block employed.

  • diastereoselective synthesis of indanes and tetralins via Intramolecular friedel crafts reaction
    Organic Letters, 2013
    Co-Authors: Jeannemarie Begouin, Francesca Capitta, Meike Niggemann
    Abstract:

    An easy access to tetralin and indane skeletons has been developed using a diastereoselective Intramolecular Friedel-Crafts Alkylation. Treatment of diastereomeric mixtures of benzyl carbinols with a catalytic amount of Ca(NTf2)2/Bu4NPF6 yields the respective tetralin or indane in good yields with high levels of regio- and diastereoselectivity.

Yuqin Zhu - One of the best experts on this subject based on the ideXlab platform.