Literature DB >> 16986975

Tandem Wittig rearrangement/aldol reactions for the synthesis of glycolate aldols.

Myra Beaudoin Bertrand1, John P Wolfe.   

Abstract

A new tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters is described. This reaction generates two carbon-carbon bonds and two contiguous stereocenters in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction conditions that do not require the use of a strong base, and the 1,2-diol products are obtained in good yield with excellent diastereoselectivity (>20:1).

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Year:  2006        PMID: 16986975     DOI: 10.1021/ol062016l

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


  4 in total

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2.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

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Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

3.  Chemoselective Palladium-Catalyzed Deprotonative Arylation/[1,2]-Wittig Rearrangement of Pyridylmethyl Ethers.

Authors:  Feng Gao; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-27       Impact factor: 9.825

4.  Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides.

Authors:  R Alan Aitken; Andrew D Harper; Ryan A Inwood; Alexandra M Z Slawin
Journal:  J Org Chem       Date:  2022-03-14       Impact factor: 4.354

  4 in total

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