Stereoselective cyclopropanation of 3-aryl-2-phosphonoacrylates induced bythe (-)-8-phenylmenthyl group as a chiral auxiliary

Authors
Takagi, R Nakamura, M Hashizume, M Kojima, S Ohkata, K
Citation
R. Takagi et al., Stereoselective cyclopropanation of 3-aryl-2-phosphonoacrylates induced bythe (-)-8-phenylmenthyl group as a chiral auxiliary, TETRAHEDR L, 42(34), 2001, pp. 5891-5895
Citations number
43
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
34
Year of publication
2001
Pages
5891 - 5895
Database
ISI
SICI code
0040-4039(20010820)42:34<5891:SCO3IB>2.0.ZU;2-T
Abstract
The cyclopropanation of (-)-8-phenylmenthyl (E)-3-aryl-2-phosphonoacrylates with dimethyloxosulfonium methylide and diazomethane afforded the correspo nding trans cyclopropane derivatives with high diastereoselectivity as the major diastereomer. The high selectivity is understandable in terms of the pi-pi interaction between the phenyl ring of the chiral auxiliary and the a crylate moiety. (C) 2001 Elsevier Science Ltd. All rights reserved.