Literature DB >> 17971984

Catalytic enantioselective stereoablative reactions: an unexploited approach to enantioselective catalysis.

Justin T Mohr1, David C Ebner, Brian M Stoltz.   

Abstract

Approaches to the preparation of enantioenriched materials via catalytic methods that destroy stereogenic elements of a molecule are discussed. Although these processes often decrease overall molecular complexity, there are several notable advantages including material recycling, enantiodivergence and convergence, and increased substrate scope. Examples are accompanied by discussion of the critical design elements required for the success of these methods.

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Year:  2007        PMID: 17971984      PMCID: PMC2963431          DOI: 10.1039/b711159m

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  19 in total

1.  Highly compatible metal and enzyme catalysts for efficient dynamic kinetic resolution of alcohols at ambient temperature.

Authors:  Belén Martín-Matute; Michaela Edin; Krisztián Bogár; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-03       Impact factor: 15.336

2.  Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides.

Authors:  Carmelo Drago; Lorenzo Caggiano; Richard F W Jackson
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-11       Impact factor: 15.336

3.  Synthesis of chiral alpha-fluoroketones through catalytic enantioselective decarboxylation.

Authors:  Masaharu Nakamura; Alakananda Hajra; Kohei Endo; Eiichi Nakamura
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-11       Impact factor: 15.336

4.  Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides.

Authors:  Forrest O Arp; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

5.  Palladium-catalyzed synthesis of substituted cycloheptane-1,4-diones by an asymmetric ring-expanding allylation (AREA).

Authors:  Sabrina R Schulz; Siegfried Blechert
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions.

Authors:  Uttam K Tambar; David C Ebner; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

7.  An experimentally derived model for stereoselectivity in the aerobic oxidative kinetic resolution of secondary alcohols by (sparteine)PdCl2.

Authors:  Raissa M Trend; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-04-14       Impact factor: 15.419

8.  Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.

Authors:  Matthew S Sigman; David R Jensen
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384

9.  Amine-salt-controlled, catalytic asymmetric conjugate addition of various amines and asymmetric protonation.

Authors:  Yoshitaka Hamashima; Hidenori Somei; Yuta Shimura; Toshihiro Tamura; Mikiko Sodeoka
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

10.  Palladium-catalyzed enantioselective oxidation of alcohols: a dramatic rate acceleration by Cs2CO3/t-BuOH.

Authors:  Jeffrey T Bagdanoff; Eric M Ferreira; Brian M Stoltz
Journal:  Org Lett       Date:  2003-03-20       Impact factor: 6.005

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  15 in total

Review 1.  Enantioselective protonation.

Authors:  Justin T Mohr; Allen Y Hong; Brian M Stoltz
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

Review 2.  Natural products as inspiration for the development of asymmetric catalysis.

Authors:  Justin T Mohr; Michael R Krout; Brian M Stoltz
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

3.  The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.

Authors:  John A Enquist; Brian M Stoltz
Journal:  Nature       Date:  2008-06-26       Impact factor: 49.962

Review 4.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

Review 5.  Protecting-group-free synthesis as an opportunity for invention.

Authors:  Ian S Young; Phil S Baran
Journal:  Nat Chem       Date:  2009-06       Impact factor: 24.427

6.  Total syntheses of cyanthiwigins B, F, and G.

Authors:  John A Enquist; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-07-18       Impact factor: 5.236

7.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

8.  Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination.

Authors:  Duy N Mai; Brandon R Rosen; John P Wolfe
Journal:  Org Lett       Date:  2011-05-10       Impact factor: 6.005

9.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

10.  The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications.

Authors:  David C Ebner; Jeffrey T Bagdanoff; Eric M Ferreira; Ryan M McFadden; Daniel D Caspi; Raissa M Trend; Brian M Stoltz
Journal:  Chemistry       Date:  2009-12-07       Impact factor: 5.236

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