Application of Rh-catalyzed cyclization for the construction of three consecutive chiral carbons in 4,9-dimethylspiro[4.4]nonane-2,7-dione

Authors
Takahashi, M Tanaka, M Sakamoto, E Imai, M Matsui, A Funakoshi, K Sakai, K Suemune, H
Citation
M. Takahashi et al., Application of Rh-catalyzed cyclization for the construction of three consecutive chiral carbons in 4,9-dimethylspiro[4.4]nonane-2,7-dione, TETRAHEDR L, 41(41), 2000, pp. 7879-7883
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
41
Year of publication
2000
Pages
7879 - 7883
Database
ISI
SICI code
0040-4039(20001007)41:41<7879:AORCFT>2.0.ZU;2-C
Abstract
Asymmetric cyclization using Rh-complexes has been applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing three consecutive chiral carbons could be stepwisely constructed fr om an identical starting material by the combination of a cationic Rh[(S)BI NAP]ClO4 and a neutral RhCl(PPh3)(3). The relationship between the stereoch emistry of the spirodiketones and the Rh-complex was also discussed. (C) 20 00 Elsevier Science Ltd. All rights reserved.