Literature DB >> 11700129

Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters.

D J Dixon1, S V Ley, A Polara, T Sheppard.   

Abstract

[reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.

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Year:  2001        PMID： 11700129     DOI： 10.1021/ol016707n

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


  2 in total

1.  The supersilyl group as a carboxylic acid protecting group: application to highly stereoselective aldol and Mannich reactions.

Authors:  Jiajing Tan; Matsujiro Akakura; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-29       Impact factor: 15.336

2.  Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

Authors:  Kanicha Sa-ei; John Montgomery
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005
  2 in total

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