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36.7.1.1.3 Method 3: Rhodium-Catalyzed Enantioselective Diboration of Alkenes

DOI: 10.1055/sos-SD-036-00589

Nativi, C.; Roelens, S.Science of Synthesis, (200836763.

In an effort to develop methodology for the asymmetric diboration of alkenes, Morken and co-workers[‌35‌] demonstrated that reactions involving chiral rhodium complexes derived from 1-[2-(diphenylphosphino)-1-naphthyl]isoquinoline (Quinap) exhibit remarkable enantioselectivity and good yields for a variety of alkenes such as (E)-prop-1-enylbenzene (12). These reactions are essentially free from competitive side reactions allowing the diboron adducts to be oxidized to the corresponding 1,2-diol 13 (Scheme 8); alternatively, they can be used as intermediates in one-pot asymmetric carbohydroxylations of alkenes via selective tandem cross couplingoxidations[‌36‌] or domino diborationhomologationoxidation reactions.[‌37‌]

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