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Asymmetric Hydroboration Chemistry

  • Chapter
Stereodirected Synthesis with Organoboranes

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 32))

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Abstract

Hydroboration provided the first nonenzymatic asymmetric synthesis of any kind to have resulted in a truly high enantioselection. The hydroboration of cis-2-butene with (−)-diisopinocampheylborane (1) derived from (+)-α-pinene proceeded with high diastereoselectivity to form the intermediate trialkylborane 2 [1, 2]. When 1 of high enantiomeric purity [3] is used and the procedure is otherwise optimized, this process yields 98% ee in the final product, (R)-(−)-2-butanol (3), which was obtained via the usual alkaline hydrogen peroxide oxidation of 2 [4]. Both enantiomers of a-pinene are readily available, and it is therefore equally simple to prepare (S)-(+)-2-butanol by this method.

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Authors and Affiliations

  1. Department of Chemistry, Washington State University, 99164-4630, Pullman, WA, USA

    Prof. Dr. Donald S. Matteson

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  1. Prof. Dr. Donald S. Matteson
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© 1995 Springer-Verlag Berlin Heidelberg

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Matteson, D.S. (1995). Asymmetric Hydroboration Chemistry. In: Stereodirected Synthesis with Organoboranes. Reactivity and Structure Concepts in Organic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-79709-5_6

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  • DOI: https://doi.org/10.1007/978-3-642-79709-5_6

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-79711-8

  • Online ISBN: 978-3-642-79709-5

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