The stereoselective crotylboration of alpha-oxocarboxylic acids

Zhe Wang, Xian Jun Meng, George Kabalka

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Crotylboronates react with alpha-oxocarboxylic acids in a highly stereocontrolled manner. The reaction presumably proceeds through a bicyclic transition state. The alpha-carboxylic substituent exerts a remarkable effect on the rate, regio- and stereoselectivities of the reaction; homoallylic alpha-hydroxycarboxylic acids are formed with regio- and stereoselectivities approach 100%.

Original languageEnglish (US)
Pages (from-to)5677-5680
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number41
DOIs
StatePublished - Oct 7 1991
Externally publishedYes

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Stereoselectivity
Regioselectivity
Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The stereoselective crotylboration of alpha-oxocarboxylic acids. / Wang, Zhe; Meng, Xian Jun; Kabalka, George.

In: Tetrahedron Letters, Vol. 32, No. 41, 07.10.1991, p. 5677-5680.

Research output: Contribution to journalArticle

Wang, Zhe ; Meng, Xian Jun ; Kabalka, George. / The stereoselective crotylboration of alpha-oxocarboxylic acids. In: Tetrahedron Letters. 1991 ; Vol. 32, No. 41. pp. 5677-5680.
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