Investigations into the enantioselective C-protonation of prostereogenic enolate(s) derived from N,N′-diisopropyl-2-phenylpropanamide using suicide C-based proton sources

12Citations
Citations of this article
2Readers
Mendeley users who have this article in their library.
Get full text

Abstract

The synthesis of enantiomerically enriched (-)-(R)-N, N′-diisopropyl- 2-phenylpropanamide was achieved in up to 69% enantiomeric excess by symmetrisation of the corresponding racemic amide by addition of sec-BuLi (to give the corresponding achiral lithium enolate) and subsequent desymmetrisation by the addition of a chiral C-based proton source. We discuss potential factors that may be responsible for this observed enantioselectivity and comment on the role of the chiral acid. © 2004 Elsevier Ltd. All rights reserved.

Cite

CITATION STYLE

APA

Coumbarides, G. S., Eames, J., Ghilagaber, S., & Suggate, M. J. (2004). Investigations into the enantioselective C-protonation of prostereogenic enolate(s) derived from N,N′-diisopropyl-2-phenylpropanamide using suicide C-based proton sources. Tetrahedron Letters, 45(51), 9469–9474. https://doi.org/10.1016/j.tetlet.2004.10.090

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free