Abstract
Matteson's asymmetric synthesis via a one-carbon homologation of the pinanediol boronic esters with (dichloromethyl)lithium at −100°C results in the insertion of a chloromethyl group into the carboncarbon bond with > 99% diastereoselectivity. This procedure makes possible the asymmetric synthesis of the chiral moiety, RR′CH ★B(OR″) 2, providing an alternative route to chiral hydroboration for these valuable chiral intermediates. Unfortunately, this method suffers from the remarkable difficulty encountered in the recovery of the pinanediol chiral auxiliary, making this asymmetric synthesis impractical. Fortunately, a systematic study of the problem has uncovered convenient procedures for the recovery of pinanediol from pinanediol boronate esters.
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