4.7 Article

A highly enantioselective approach towards optically active γ-amino alcohols by tin-catalyzed kinetic resolution of 1,3-amino alcohols

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 53, Pages 7392-7395

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc01963a

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Funding

  1. National Natural Science Foundation of China [21772086]

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A highly enantioselective kinetic resolution of racemic 1,3-amino alcohols via O-Acylation was achieved using a chiral organotin catalyst. The reaction showed excellent efficiency and high enantioselectivity, with better selectivity for anti-1,3-amino alcohols.
A highly enantioselective kinetic resolution of racemic 1,3-amino alcohols via O-Acylation was achieved using a chiral organotin as the catalyst. Alkyl- and aryl-substituted 1,3-amino alcohols were resolved with excellent efficiencies to afford the recovered 1,3-amino alcohols and acylative products with high enantioselectivities, with s factors up to >600. Notably, the chiral organotin catalyst was more selective for anti-1,3-amino alcohols than for syn-isomers. A Gram-scale reaction with loading using 2 mol% catalysts demonstrated the utility of this protocol.

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