A straightforward route to enantiopure alpha-substituted derivatives of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.

Tetrahedron
Francisco J SayagoCarlos Cativiela

Abstract

High yielding and remarkably selective alkylations of a suitably protected derivative of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid are described. The fused bicyclic structure of this proline analogue greatly influences the stereochemical outcome of direct alkylation reactions taking place at the alpha-carbon and provides access to alpha-substituted analogues with retention of the configuration. The overall procedure allows the preparation of enantiopure alpha-substituted derivatives of this Oic isomer, suitably protected for their incorporation into peptides, in a straightforward manner.

References

Jan 1, 1997·Biopolymers·V J HrubyM Shenderovich
May 12, 2004·Peptides·John M Stewart
Dec 24, 2005·Expert Opinion on Pharmacotherapy·K Alfakih, A S Hall
Dec 13, 2006·Cellular and Molecular Life Sciences : CMLS·J Gass, C Khosla
Jan 2, 2007·Neuropeptides·J A García-HorsmanJ I Venäläinen
Dec 17, 2009·Tetrahedron, Asymmetry·Francisco J SayagoCarlos Cativiela
Jan 28, 2010·Tetrahedron, Asymmetry·Sergio Alatorre-SantamaríaVicente Gotor

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Citations

Oct 25, 2012·The Journal of Organic Chemistry·Corey H BaschGlenn P A Yap
Jun 26, 2015·Chemistry : a European Journal·Alejandro GutiérrezM Concepción Gimeno

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