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Asymmetric Lithiation−Substitution of Amines Involving Rearrangement of Borates

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journal contribution
posted on 03.01.2008, 00:00 by Iain Coldham, Jignesh J. Patel, Sophie Raimbault, David T. E. Whittaker, Harry Adams, Guang Y. Fang, Varinder K. Aggarwal
Asymmetric lithiation of substituted benzylamines, N-Boc-pyrrolidine, or N-Boc-indoline using Beak's methodology was followed by electrophilic quench with trialkylboranes. The resulting borate intermediates rearrange with concomitant C−N bond breakage to give, after oxidation, chiral secondary alcohols with high enantioselectivity.