AZIRIDINATION OF STYRENE DERIVATIVES WITH 3-ACETOXYAMINOQUINAZOLINONES - PROBING TRANSITION-STATE GEOMETRY FROM CHANGES IN DIASTEREOSELECTIVITY

Authors
ATKINSON RS CLAXTON TA LOCHRIE IST ULUKANLI S
Citation
Rs. Atkinson et al., AZIRIDINATION OF STYRENE DERIVATIVES WITH 3-ACETOXYAMINOQUINAZOLINONES - PROBING TRANSITION-STATE GEOMETRY FROM CHANGES IN DIASTEREOSELECTIVITY, Tetrahedron letters, 39(28), 1998, pp. 5113-5116
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
28
Year of publication
1998
Pages
5113 - 5116
Database
ISI
SICI code
0040-4039(1998)39:28<5113:AOSDW3>2.0.ZU;2-8
Abstract
In aziridinations of beta-substituted styrenes (4), (5) and (6) with t he enantiopure 3-acetoxyaminoquinazolinone (1), diastereoselectivity ( dr) increases from 5:1 for 6) to 10:1 (for (10) to similar to 20:1 (fo r (11)): changes in transition state geometry which account for this i ncrease are rationalised using Frontier;Orbital Theory. (C) 1998 Elsev ier Science Ltd. All rights reserved.