Module 3 : Organometallic Reagents

Lecture 25 : Organoboranes

 

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Examples:

G. W. Kabalka, S. Yu, N.-S. Li, Tetrahedron Lett. 1997, 38, 5455.

D.L. Gober, R. A. Lerner, B. F. Cravatt, J. Org. Chem. 1994, 59, 5078.


3.5.2 Reactions of Alkylboranes
3.5.2.1 Synthesis of Alcohols


The transformation of alkenes to alcohols proceeds with complete retention of configuration at the boron-bearing carbon (Scheme 2).

Scheme 2


Asymmetric hydroboration of alkenes can be carried out using chiral boranes with excellent enantioselectivity (Scheme 3).

Scheme 3