A new synthesis of 2,5-disubstituted N-acylpyrrolidines through an S(N)2' reaction promoted by the nitrogen anion of a secondary amide onto an allylic bromide is reported. A moderate stereoselectivity, in favour of the trans heterocycle, was observed during the cyclization of a chiral precursor, while a good stereoselectivity, this time in favour of the cis one, was obtained when the second stereocentre was introduced after the cyclization step to give the same product. (c) 2006 Elsevier Ltd. All rights reserved.
A new convergent and stereoselective synthesis of 2,5-disubstituted N-acylpyrrolidines
BANFI, LUCA;BASSO, ANDREA;GUANTI, GIUSEPPE;RIVA, RENATA
2006-01-01
Abstract
A new synthesis of 2,5-disubstituted N-acylpyrrolidines through an S(N)2' reaction promoted by the nitrogen anion of a secondary amide onto an allylic bromide is reported. A moderate stereoselectivity, in favour of the trans heterocycle, was observed during the cyclization of a chiral precursor, while a good stereoselectivity, this time in favour of the cis one, was obtained when the second stereocentre was introduced after the cyclization step to give the same product. (c) 2006 Elsevier Ltd. All rights reserved.
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