Highly efficient asymmetric access to 1-azaspiro [4.4] nonane skeleton

L Planas, J Pérard-Viret, J Royer, M Selkti, A Thomas

Index: Planas, Loic; Perard-Viret, Joelle; Royer, Jacques; Selkti, Mohamed; Thomas, Alain Synlett, 2002 , # 10 p. 1629 - 1632

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Citation Number: 14

Abstract

We anticipated that this could be possible by the use of chiral non racemic α,β-unsaturated γ-lactams 3 that we have been developing for some years. [2] The possibility to diastereoselectively substitute γ-lactams 3 at the C-5 position with either an electrophile [via the silyloxypyrrole, path (a)] or a nucleophile [via a N-acyliminium, path (b), Scheme [2] ], permits to construct a quaternary spiro center at this carbon. As a matter of fact, the application of path (a) maintains the α,β- ...