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. 2014 Jul 2;136(26):9264-7.
doi: 10.1021/ja504228p. Epub 2014 Jun 24.

Hydroxyl-directed stereoselective diboration of alkenes

Thomas P Blaisdell  1 , Thomas C Caya, Liang Zhang, Amparo Sanz-Marco, James P Morken
Affiliations

Hydroxyl-directed stereoselective diboration of alkenes

Thomas P Blaisdell et al. J Am Chem Soc. .

Abstract

An alkoxide-catalyzed directed diboration of alkenyl alcohols is described. This reaction occurs in a stereoselective fashion and is demonstrated with cyclic and acyclic homoallylic and bishomoallylic alcohol substrates. After oxidation, the reaction generates 1,2-diols such that the process represents a method for the stereoselective directed dihydroxylation of alkenes.

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Figures

Figure 1
Figure 1
Directed diboration of alkenyl alcohols.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

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