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.

10.4.2 Reactions of Alkylboranes

10.4.2.1 Oxidation to Alcohols

Hydroboration and oxidative strategy provides an effective route for the transformation of alkenes to alcohols with retention of configuration at the boron-bearing carbon (Scheme 4).

Scheme 4

Asymmetric version of this process has made a remarkable progress using chiral boranes with excellent enantioselectivity (Scheme 5).

Scheme 5

Alkylboranes also undergo isomerization on heating to give products that contain the boron atom at the least hindered position of the alkyl chain (Scheme 6).

Scheme 6