Literature DB >> 15070342

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

Raissa M Trend1, Brian M Stoltz.   

Abstract

A model for asymmetric induction in palladium-catalyzed aerobic oxidative kinetic resolution is described. The model is based on coordination complexes and general reactivity trends of the parent (sp)PdCl2 catalyst. The first example of a nonracemic chiral palladium alkoxide complex is presented, and exhibits the subtle steric influences of the C1 symmetric ligand sparteine.

Entities:  

Year:  2004        PMID： 15070342     DOI： 10.1021/ja039551q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

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

Authors:  Justin T Mohr; David C Ebner; Brian M Stoltz
Journal:  Org Biomol Chem       Date:  2007-10-01       Impact factor: 3.876

2.  Palladium-catalyzed enantioselective oxidation of chiral secondary alcohols: access to both enantiomeric series.

Authors:  David C Ebner; Raissa M Trend; Cédric Genet; Matthew J McGrath; Peter O'Brien; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: applications to the total synthesis of alkaloids.

Authors:  Shyam Krishnan; Jeffrey T Bagdanoff; David C Ebner; Yeeman K Ramtohul; Uttam K Tambar; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

4.  Enantiomeric impurities in chiral synthons, catalysts, and auxiliaries. Part 3.

Authors:  Ke Huang; Zachary S Breitbach; Daniel W Armstrong
Journal:  Tetrahedron Asymmetry       Date:  2006-10-27

5.  Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation.

Authors:  Raissa M Trend; Yeeman K Ramtohul; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

6.  Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

7.  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

8.  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

9.  Elucidating the significance of beta-hydride elimination and the dynamic role of acid/base chemistry in a palladium-catalyzed aerobic oxidation of alcohols.

Authors:  Jaime A Mueller; Christopher P Goller; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419

10.  Use of a palladium(II)-catalyzed oxidative kinetic resolution in synthetic efforts toward bielschowskysin.

Authors:  Michael E Meyer; John H Phillips; Eric M Ferreira; Brian M Stoltz
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457
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