Studies on the asymmetric cycloaddition of 2-azaallyl anions with alkenes

Authors
Pearson, WH Stevens, EP Aponick, A
Citation
Wh. Pearson et al., Studies on the asymmetric cycloaddition of 2-azaallyl anions with alkenes, TETRAHEDR L, 42(42), 2001, pp. 7361-7365
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
42
Year of publication
2001
Pages
7361 - 7365
Database
ISI
SICI code
0040-4039(20011015)42:42<7361:SOTACO>2.0.ZU;2-U
Abstract
A preliminary survey of strategies for the asymmetric cycloaddition of nons tabilized 2-azaallyllithiums with alkenes is reported. The chiral diamine ( -)-sparteine exerted little, if any, absolute stereocontrol. The attachment of a chiral auxiliary to the anion was more successful, leading to the fir st example of an asymmetric cycloaddition of a 2-azaallyllithium (24 to 25, 98% e.e.). (C) 2001 Elsevier Science Ltd. All rights reserved.