Hydroxyl-Directed Stereoselective Diboration of Alkenes

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 represe...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 136; no. 26; pp. 9264 - 9267
Main Authors Blaisdell, Thomas P, Caya, Thomas C, Zhang, Liang, Sanz-Marco, Amparo, Morken, James P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.07.2014
Amer Chemical Soc
Subjects
Alcohols - chemistry
Alkenes - chemistry
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Communication
Hydroxyl Radical
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
ALCOHOLS
ORGANIC-SYNTHESIS
DIHYDROXYLATION
HYDROBORATION
F-RING
CATALYZED ENANTIOSELECTIVE DIBORATION
CONJUGATE ADDITIONS
SPONGISTATIN-1
INTRAMOLECULAR BIS-SILYLATION
SUBUNIT
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Summary: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.
Bibliography:NIH RePORTER
ISSN:0002-7863
1520-5126
DOI:10.1021/ja504228p