Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF3 moiety

Ralph Husmann; Erli Sugiono; Stefanie Mersmann; Gerhard Raabe; Magnus Rueping; Carsten Bolm

doi:10.1021/ol103093r

Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF3 moiety

Org Lett. 2011 Mar 4;13(5):1044-7. doi: 10.1021/ol103093r. Epub 2011 Jan 24.

Authors

Ralph Husmann¹, Erli Sugiono, Stefanie Mersmann, Gerhard Raabe, Magnus Rueping, Carsten Bolm

Affiliation

¹ Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany.

PMID: 21348534
DOI: 10.1021/ol103093r

Abstract

A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis
Amino Acids / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Indoles / chemical synthesis*
Indoles / chemistry*
Molecular Structure
Organophosphates / chemistry*
Stereoisomerism

Substances

Amino Acids
Hydrocarbons, Fluorinated
Indoles
Organophosphates