Lithium Ephedrinate Mediated Aldol Reaction of Arylacetonitriles: Thermodynamic Control of Enantioselectivity.

Angew Chem Int Ed Engl

Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (China), Fax: (+852) 2358-1594.

Published: September 1998

Deracemization, the conversion of a racemic mixture into an enantiomerically enriched material, is achieved with the retro-aldol reaction of rac-1 in the presence of lithium (-)-ephedrinate [Eq. (1)]. Remarkably, two stereogenic centers are simultaneously deracemized. This reaction shows that efficient thermodynamic control of the enantioselectivity of aldol reactions is possible.

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http://dx.doi.org/10.1002/(SICI)1521-3773(19980904)37:16<2252::AID-ANIE2252>3.0.CO;2-ZDOI Listing

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