Stereoselective allyl- and crotylboration of alpha-hydroxyketones via neighboring group control

Zhe Wang, Xian Jun Meng, George Kabalka

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Allylboronates and crotylboronates react with alpha-hydroxyketones to yield tertiary homoallylic alcohols in a highly stereocontrolled manner. The reaction presumably proceeds via a rigid bicyclic transition state. The alpha-hydroxy substituent exerts a remarkable and predictable effect on the diastereoselectivity of the reaction. Homoallylic alcohols are formed with diastereoselectivities approaching 100%.

Original languageEnglish (US)
Pages (from-to)1945-1948
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number17
DOIs
StatePublished - Apr 22 1991
Externally publishedYes

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Alcohols
Control Groups

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereoselective allyl- and crotylboration of alpha-hydroxyketones via neighboring group control. / Wang, Zhe; Meng, Xian Jun; Kabalka, George.

In: Tetrahedron Letters, Vol. 32, No. 17, 22.04.1991, p. 1945-1948.

Research output: Contribution to journalArticle

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