15277-97-1Relevant articles and documents
COMPOSITIONS AND METHODS FOR REDUCTION OF KETONES, ALDEHYDES AND IMINIUMS, AND PRODUCTS PRODUCED THEREBY
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Paragraph 0073-0074, (2018/01/20)
A method of producing an alcohol, comprises reducing an aldehyde or a ketone with a hydridosilatrane. The reducing is carried out with an activator.
Organoboranes. LI. Convenient procedures for the recovery of pinanediol in asymmetric synthesis via one-carbon homologation of boronic esters
Brown, Herbert C.,Rangaishenvi, Milind V.
, p. 15 - 30 (2007/10/02)
Matteson's asymmetric synthesis via a one-carbon homologation of the pinanediol boronic esters with (dichloromethyl)litihium at -100 deg C results in the insertion of a chloromethyl group into the carbon-carbon bond with > 99percent 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 pianendiol boronate esters