Journal
TETRAHEDRON
Volume 57, Issue 31, Pages 6713-6719Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00619-6
Keywords
absolute asymmetric synthesis; solid-state; photochemical reaction; chiral crystal; beta-lactam
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Achiral N-methacryloylthiobenzanilide formed (Z,E)-conformation of the imide moiety and crystallized in a chiral fashion. The solid-state photoreaction gave optically active beta -lactam. The dynamic molecular rearrangement for cyclization was elucidated on the basis of direct comparison of the absolute configuration of both the starting material and the photoproduct. Crystal-to-crystal transformation was observed in the photoreaction of the (E,E)-conformation of N-isopropyl-N-tigloylthiobenzamide, which needs small atomic rearrangement for the cyclization and gave thietane stereo- and chemo-selectively. (C) 2001 Elsevier Science Ltd. All rights reserved.
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