Literature DB >> 19947622

Catalytic enantioselective formation of chiral-bridged dienes which are themselves ligands for enantioselective catalysis.

M Kevin Brown1, E J Corey.   

Abstract

This paper reports a method for highly enantioselective Diels-Alder reaction with an acetylene equivalent to produce chiral-bridged dienes. These dienes, by coordination to Rh(I), can serve as catalysts for the enantioselective addition of vinyl or aryl groups to alpha,beta-unsaturated ketones.

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Year:  2010        PMID： 19947622      PMCID： PMC2814301          DOI： 10.1021/ol9025793

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  21 in total

1.  Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions.

Authors:  Tamio Hayashi; Kaori Yamasaki
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions.

Authors:  Thomas Gendrineau; Olivier Chuzel; Hendrik Eijsberg; Jean-Pierre Genet; Sylvain Darses
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

4.  Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids. Arylrhodium, oxa-pi-allylrhodium, and hydroxorhodium intermediates.

Authors:  Tamio Hayashi; Makoto Takahashi; Yoshiaki Takaya; Masamichi Ogasawara
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

5.  Enantioselective catalysis based on cationic oxazaborolidines.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Cationic-oxazaborolidine-catalyzed enantioselective Diels-Alder reaction of alpha,beta-unsaturated acetylenic ketones.

Authors:  Joshua N Payette; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Tuning the chiral environment of C2-symmetric diene ligands: development of 3,7-disubstituted bicyclo[3.3.1]nona-2,6-dienes.

Authors:  Ryo Shintani; Yoshitaka Ichikawa; Keishi Takatsu; Fu-Xue Chen; Tamio Hayashi
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

8.  Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors.

Authors:  Christian Defieber; Jean-François Paquin; Sonia Serna; Erick M Carreira
Journal:  Org Lett       Date:  2004-10-14       Impact factor: 6.005

9.  Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): catalytic, kinetic resolution of allyl carbonates.

Authors:  Christian Fischer; Christian Defieber; Takeyuki Suzuki; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

10.  Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions.

Authors:  Kazuhiro Okamoto; Tamio Hayashi; Viresh H Rawal
Journal:  Org Lett       Date:  2008-09-05       Impact factor: 6.005
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  5 in total

1.  Cobalt-mediated, enantioselective synthesis of C(2) and C(1) dienes.

Authors:  W Christopher Boyd; Mark R Crimmin; Lauren E Rosebrugh; Jennifer M Schomaker; Robert G Bergman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-10-29       Impact factor: 15.419

2.  Sequential aldol condensation-transition metal-catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids.

Authors:  Yuan-Xi Liao; Chun-Hui Xing; Matthew Israel; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2011-03-18       Impact factor: 6.005

Review 3.  Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

Authors:  Martin J Schnermann; Ryan A Shenvi
Journal:  Nat Prod Rep       Date:  2015-04       Impact factor: 13.423

4.  Retracted Article: Synthesis of deuterated isopentyl pyrophosphates for chemo-enzymatic labelling methods: GC-EI-MS based 1,2-hydride shift in epicedrol biosynthesis.

Authors:  Madhukar S Said; Govinda R Navale; Jayant M Gajbhiye; Sandip S Shinde
Journal:  RSC Adv       Date:  2019-09-09       Impact factor: 4.036

5.  Tandem Aldol Condensation - Platinacycle-Catalyzed Addition Reactions of Aldehydes, Methyl Ketones and Arylboronic Acids.

Authors:  Yuan-Xi Liao; Qiao-Sheng Hu
Journal:  European J Org Chem       Date:  2012-09-05
  5 in total

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