Asymmetric lithiation-substitution of amines involving rearrangement of borates |
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| Authors: | Coldham Iain Patel Jignesh J Raimbault Sophie Whittaker David T E Adams Harry Fang Guang Y Aggarwal Varinder K |
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| Institution: | Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. i.coldham@sheffield.ac.uk |
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| Abstract: | 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. |
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