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A new lithium alkoxide accelerated diastereoselective cyanation of ketones
H S Wilkinson1, P T Grover, C P Vandenbossche
1Chemical Research and Development, Sepracor Inc., 111 Locke Drive, Marlborough, Massachusetts 01752, USA.
Organic Letters
|February 17, 2001
Abstract:
[reaction: see text] A remarkably general lithium heteroatom assisted TMSCN or TBSCN addition to aldehydes and ketones has been discovered. The process provides excellent selectivities and high rates. Conformationally constrained ketones such as camphor, fenchone, and nopinone give excellent diastereoselectivities with TMSCN. Reduction of 2 provided diastereopure amino alcohol 3 in good yield. alpha- and beta-Methyl cyclohexanones with TBSCN-LiOR afford high diastereoselectivities and yields.