1,2-asymmetric induction in the ketene Claisen rearrangement of (2S,3E)-5-(isopropylsulfanyl)-3-pentenes

Authors
Gonda, J Martinkova, M Ernst, B Bellus, D
Citation
J. Gonda et al., 1,2-asymmetric induction in the ketene Claisen rearrangement of (2S,3E)-5-(isopropylsulfanyl)-3-pentenes, TETRAHEDRON, 57(26), 2001, pp. 5607-5613
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
26
Year of publication
2001
Pages
5607 - 5613
Database
ISI
SICI code
0040-4020(20010625)57:26<5607:1IITKC>2.0.ZU;2-B
Abstract
The ketene Claisen rearrangement of chiral (2S,3E)-5-(isopropylsulfanyl)-3- penten-2 has been investigated by the semiempirical AMI method. The observe d efficient direction of the 1,2-asymmetric induction in the ketene Claisen rearrangement has been modelled from comparison of the energies of the fou r possible transition stares arising from two chair-like and two boat-like structures. The resulting trends of relative transition state energy are in reasonable agreement with experimental observations. (C) 2001 Elsevier Sci ence Ltd. All rights reserved.