Literature DB >> 11922799

Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones.

David A Evans1, C Wade Downey, Jared T Shaw, Jason S Tedrow.   

Abstract

[reaction: see text] Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2.OEt2 in the presence of triethylamine and chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 11922799     DOI： 10.1021/ol025553o

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


  14 in total

1.  Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors:  Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

2.  Enantioselective Synthesis of Dilignol Model Compounds and Their Stereodiscrimination Study with a Dye-Decolorizing Peroxidase.

Authors:  Gaochao Huang; Ruben Shrestha; Kaimin Jia; Brian V Geisbrecht; Ping Li
Journal:  Org Lett       Date:  2017-03-22       Impact factor: 6.005

3.  Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a.

Authors:  Michael T Crimmins; Anne-Marie R Dechert
Journal:  Org Lett       Date:  2012-04-18       Impact factor: 6.005

4.  Symbiotic reagent activation: Oppenauer oxidation of magnesium alkoxides by silylglyoxylates triggers second-stage aldolization.

Authors:  Xin Linghu; Andrew D Satterfield; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2006-07-26       Impact factor: 15.419

5.  Vinylogous Dehydration by a Polyketide Dehydratase Domain in Curacin Biosynthesis.

Authors:  William D Fiers; Greg J Dodge; David H Sherman; Janet L Smith; Courtney C Aldrich
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

6.  Enantioselective total synthesis of (-)-pironetin: iterative aldol reactions of thiazolidinethiones.

Authors:  Michael T Crimmins; Anne-Marie R Dechert
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

7.  Stereoselective Synthesis of Baulamycin A.

Authors:  Jonathan R Thielman; David H Sherman; Robert M Williams
Journal:  J Org Chem       Date:  2020-02-07       Impact factor: 4.354

8.  A Useful Modification of the Evans Magnesium Halide-Catalyzed anti-Aldol Reaction: Application to Enolizable Aldehydes.

Authors:  Aaron E May; Nathan T Connell; Heidi A Dahlmann; Thomas R Hoye
Journal:  Synlett       Date:  2010       Impact factor: 2.454

9.  Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin.

Authors:  David S Huang; Henry L Wong; Gunda I Georg
Journal:  ChemMedChem       Date:  2017-03-22       Impact factor: 3.466

10.  Intramolecular ring-opening from a CO2-derived nucleophile as the origin of selectivity for 5-substituted oxazolidinone from the (salen)Cr-catalyzed [aziridine + CO2] coupling.

Authors:  Debashis Adhikari; Aaron W Miller; Mu-Hyun Baik; SonBinh T Nguyen
Journal:  Chem Sci       Date:  2014-11-21       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.