Literature DB >> 14748604

Alpha,alpha-disubstituted boron enolates in the asymmetric synthesis of quaternary carbon centers.

E Diane Burke1, James L Gleason.   

Abstract

[reaction: see text] Reduction of alpha,alpha-disubstituted thioglycolate amides with lithium di-tert-butylbiphenylide affords alpha,alpha-disubstituted enolates with high Z/E selectivity. Transmetalation of the enolates with dicyclohexylboron bromide facilitates highly diastereoselective aldol reaction with aromatic and alpha,beta-unsaturated aldehydes.

Entities:  

Year:  2004        PMID： 14748604     DOI： 10.1021/ol0364428

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


  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.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

3.  Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.

Authors:  Zackaria Nairoukh; Gunda G K S Narayana Kumar; Yury Minko; Ilan Marek
Journal:  Chem Sci       Date:  2016-09-15       Impact factor: 9.825
  3 in total

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