Organic Letters p. 553 - 556 (2001)
Update date:2022-07-30
Topics:
Wilkinson, H. Scott
Grover, Paul T.
Vandenbossche, Charles P.
Bakale, Roger P.
Bhongle, Nandkumar N.
Wald, Stephen A.
Senanayake, Chris H.
(Matrix presented) 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. α- and β-Methyl cyclohexanones with TBSCN-LiOR afford high diastereoselectivities and yields.
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(2001)Doi:10.1021/jo00065a021
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(2001)
