Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

SG Davies, AM Fletcher, PM Roberts, AD Smith

Index: Davies, Stephen G.; Fletcher, Ai M.; Roberts, Paul M.; Smith, Andrew D. Tetrahedron, 2009 , vol. 65, # 49 p. 10192 - 10213

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Citation Number: 66

Abstract

Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl) amide or lithium (R)-N-but-3- enyl-N-(α-methylbenzyl) amide to an alkyl hexa-2, 4-dienoate or alkyl hepta-2, 6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the ...