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Dynamic thermodynamic resolution: solvent effects, mechanism, and an asymmetric 3,4,5-substituted benzazepine synthesis.

Park YS, Yum EK, Basu A, Beak P

Department of Chemistry, Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 61801, USA.

[reaction: see text] The resolution in the lithiation-substitution sequence from 1 to 4-11 in MTBE is shown to be under thermodynamic control in contrast to the previous report of kinetic control in diethyl ether. Diastereomeric equilibration of a soluble complex is shown to be controlling and an asymmetric synthesis of a 3,4,5-substituted benzazepine is reported.

Published 15 June 2006 in Org Lett, 8(13): 2667-70.
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