Literature DB >> 26823643

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

Aaron E May1, Nathan T Connell1, Heidi A Dahlmann1, Thomas R Hoye1.   

Abstract

A practical protocol for use of the magnesium halide-catalyzed anti-aldol reaction of an Evans N-acyloxazolidinone with enolizable aldehydes is reported. The yields of anti-aldol adducts for saturated or unsaturated and branched or unbranched aliphatic aldehydes are preparatively useful.

Entities:  

Keywords:  Aldol reaction; aldehydes; catalysis; halides

Year:  2010        PMID： 26823643      PMCID： PMC4727177          DOI： 10.1055/s-0030-1258480

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  11 in total

1.  The first direct and enantioselective cross-aldol reaction of aldehydes.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

2.  Total synthesis of piericidin A1 and B1 and key analogues.

Authors:  Martin J Schnermann; F Anthony Romero; Inkyu Hwang; Eiko Nakamaru-Ogiso; Takao Yagi; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

3.  Lewis base activation of lewis acids. Addition of silyl ketene acetals to aldehydes.

Authors:  Scott E Denmark; Thomas Wynn; Gregory L Beutner
Journal:  J Am Chem Soc       Date:  2002-11-13       Impact factor: 15.419

4.  Highly diastereofacial anti-aldol reaction: practical synthesis of optically active anti-2-alkyl-3-hydroxycarboxylic acid ester units.

Authors:  M Kurosu; M Lorca
Journal:  J Org Chem       Date:  2001-02-23       Impact factor: 4.354

5.  Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts. Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts.

Authors:  Yasuhiro Yamashita; Haruro Ishitani; Haruka Shimizu; Shū Kobayashi
Journal:  J Am Chem Soc       Date:  2002-04-03       Impact factor: 15.419

6.  Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones.

Authors:  David A Evans; Jason S Tedrow; Jared T Shaw; C Wade Downey
Journal:  J Am Chem Soc       Date:  2002-01-23       Impact factor: 15.419

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

Authors:  David A Evans; C Wade Downey; Jared T Shaw; Jason S Tedrow
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

8.  Pectenotoxin-2 synthetic studies. 1. Alkoxide precoordination to [Rh(NBD)(DIPHOS-4)]BF(4) allows directed hydrogenation of a 2,3-dihydrofuran-3-ol without competing furan production.

Authors:  Leo A Paquette; Xiaowen Peng; Dmitriy Bondar
Journal:  Org Lett       Date:  2002-03-21       Impact factor: 6.005

9.  Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines.

Authors:  Aaron E May; Patrick H Willoughby; Thomas R Hoye
Journal:  J Org Chem       Date:  2008-03-18       Impact factor: 4.354

10.  Highly diastereoselective anti-aldol reactions utilizing the titanium enolate of cis-2-arylsulfonamido-1- acenaphthenyl propionate.

Authors:  Arun K Ghosh; Jae-Hun Kim
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005
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  1 in total

1.  Structure-Reactivity Relationships in Lithiated Evans Enolates: Influence of Aggregation and Solvation on the Stereochemistry and Mechanism of Aldol Additions.

Authors:  Evan H Tallmadge; Janis Jermaks; David B Collum
Journal:  J Am Chem Soc       Date:  2015-12-24       Impact factor: 15.419
  1 in total

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