The intermolecular enamine catalyzed asymmetric ‘formal’ alpha-alkylation of aldehydes is described. The novel approach is founded upon the use of an alkylating reagent able to generate an highly stabilized carbocation which can readily intercept the enamine intermediate. Notably, L-proline proved the best catalyst, providing an easy route to relevant 3-indolyl derivatives 2 with high diastereo- and enantiocontrol.

Proline Catalyzed Asymmetric Formal alpha-Alkylation of Aldehydes via Vinylogous Iminium Ion Intermediate Generated from Arylsulfonyl Indoles

SHAIKH, RAFIK RAJJAK;PETRINI, Marino;
2008-01-01

Abstract

The intermolecular enamine catalyzed asymmetric ‘formal’ alpha-alkylation of aldehydes is described. The novel approach is founded upon the use of an alkylating reagent able to generate an highly stabilized carbocation which can readily intercept the enamine intermediate. Notably, L-proline proved the best catalyst, providing an easy route to relevant 3-indolyl derivatives 2 with high diastereo- and enantiocontrol.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/102676
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