Diastereoselective synthesis of a key intermediate for the preparation of tricyclic beta-lactam antibiotics

Authors
Matsumoto, T Murayama, T Mitsuhashi, S Miura, T
Citation
T. Matsumoto et al., Diastereoselective synthesis of a key intermediate for the preparation of tricyclic beta-lactam antibiotics, TETRAHEDR L, 40(27), 1999, pp. 5043-5046
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
27
Year of publication
1999
Pages
5043 - 5046
Database
ISI
SICI code
0040-4039(19990702)40:27<5043:DSOAKI>2.0.ZU;2-I
Abstract
Asymmetric synthesis of (S)-5 has been accomplished with an excellent enant iomeric hydrogenation of racemic 5 using ruthenium-BINAP-diamine-KOH system , followed by oxidation. Magnesium enolate of (2S)-2-methoxycyclohexanone [ (S)-5] reacts with the 4-acetoxyazetidinone 4 to give the key intermediate 3 viith high yield and diastereoselectivity for the synthesis of sanfetrine m 1. (C) 1999 Elsevier Science Ltd. All rights reserved.