In:
European Journal of Organic Chemistry, Wiley, Vol. 2006, No. 18 ( 2006-09), p. 4214-4223
Abstract:
Series of enantiomerically pure 3‐alkenylpyrrolidines, substituted azepanes and stereodefined aminoalkenes were synthesized from 2‐alkenylazetidinium trifluoromethanesulfonate salts. The high chemoselectivity of these reactions was found to be strongly dependent both on the nature of the base involved in the process (PhLi or KHMDS) and on the relative cis or trans stereochemistry of the intermediate ammonium ylide. When the ylide and the adjacent alkene are trans , a [1,2] sigmatropic shift occurs exclusively, producing a pyrrolidine with high levels of regioselectivity. On the other hand, clean conversion into 4,5‐dehydroazepanes through a [2,3] sigmatropic shift is observed when these two groups are in a cis relationship.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2006:18
DOI:
10.1002/ejoc.200600362
Language:
English
Publisher:
Wiley
Publication Date:
2006
detail.hit.zdb_id:
1475010-7
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