Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

Authors
Bragg, RA Clayden, J
Citation
Ra. Bragg et J. Clayden, Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations, TETRAHEDR L, 40(48), 1999, pp. 8323-8326
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
48
Year of publication
1999
Pages
8323 - 8326
Database
ISI
SICI code
0040-4039(19991126)40:48<8323:SFOTCF>2.0.ZU;2-V
Abstract
Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N -substituents (such as alpha-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cy clisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the p roduct. Highly substituted pyrrolidinone rings may be formed as single enan tiomers from enantiomerically pure starting materials. (C) 1999 Elsevier Sc ience Ltd. All rights reserved.