Auxiliary induced asymmetric Michael-aldol reaction under kinetic and thermodynamic conditions

Authors
Takasu, K Ueno, M Ihara, M
Citation
K. Takasu et al., Auxiliary induced asymmetric Michael-aldol reaction under kinetic and thermodynamic conditions, TETRAHEDR L, 41(13), 2000, pp. 2145-2148
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
13
Year of publication
2000
Pages
2145 - 2148
Database
ISI
SICI code
0040-4039(20000327)41:13<2145:AIAMRU>2.0.ZU;2-O
Abstract
Asymmetric intramolecular Michael-aldol reaction of (-)-phenylmenthyl enoat es 1 affords tricyclic cyclobutanes 2 in excellent diastereoselectivity. It is made clear that Michael-aldol reaction is reversible under conditions u sing trimethylsilyl iodide (TMSI) in the presence of hexamethyldisilazane ( HMDS) at ambient temperature. The difference of stereoselectivity under kin etic or thermodynamic conditions are reported. (C) 2000 Elsevier Science Lt d. Ail rights reserved.