Literature DB >> 23885946

(Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: enantioselective synthesis of anti-aldols.

Christophe Allais1, Philippe Nuhant, William R Roush.   

Abstract

The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-α-methyl-β-hydroxy esters 9 or 10 with excellent diastereo- (up to ≥20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.

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Year:  2013        PMID： 23885946      PMCID： PMC3773495          DOI： 10.1021/ol401679g

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


  27 in total

Review 1.  Catalytic asymmetric tandem transformations triggered by conjugate additions.

Authors:  Hong-Chao Guo; Jun-An Ma
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-09       Impact factor: 15.336

2.  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

3.  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

4.  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

5.  Highly stereoselective and scalable anti-aldol reactions using N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: scope and origins of stereoselectivities.

Authors:  Hua Yang; Subham Mahapatra; Paul Ha-Yeon Cheong; Rich G Carter
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

6.  Direct organocatalytic asymmetric aldol reactions of alpha-amino aldehydes: expedient syntheses of highly enantiomerically enriched anti-beta-hydroxy-alpha-amino acids.

Authors:  Rajeswari Thayumanavan; Fujie Tanaka; Carlos F Barbas III
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

7.  Anti aldol selectivity in a synthetic approach to the C1-C12 fragment of the tedanolides.

Authors:  Michael E Jung; Ting-hu Zhang
Journal:  Org Lett       Date:  2007-12-08       Impact factor: 6.005

8.  Diisopinocampheylborane-mediated reductive aldol reactions: highly enantio- and diastereoselective synthesis of syn aldols from N-acryloylmorpholine.

Authors:  Philippe Nuhant; Christophe Allais; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-01       Impact factor: 15.336

9.  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

10.  Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts.

Authors:  Takushi Shiomi; Takahiro Adachi; Jun-ichi Ito; Hisao Nishiyama
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005
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  3 in total

1.  Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors:  Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

2.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

3.  Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.

Authors:  Jeremy Kister; Daniel H Ess; William R Roush
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005
  3 in total

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