Synlett 2016; 27(01): 6-10
DOI: 10.1055/s-0035-1560813
letter
© Georg Thieme Verlag Stuttgart · New York

Cation-Directed Enantioselective N-Functionalization of Pyrroles

Roly J. Armstrong
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   URL: http://msmith.chem.ox.ac.uk/   eMail: martin.smith@chem.ox.ac.uk
,
Melissa D’Ascenzio
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   URL: http://msmith.chem.ox.ac.uk/   eMail: martin.smith@chem.ox.ac.uk
,
Martin D. Smith*
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK   URL: http://msmith.chem.ox.ac.uk/   eMail: martin.smith@chem.ox.ac.uk
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 17. September 2015

Accepted after revision: 14. Oktober 2015

Publikationsdatum:
05. November 2015 (online)


Preview

Dedicated to Prof. Steven V. Ley on the occasion of his 70th birthday

Abstract

A catalytic enantioselective N-functionalization of pyrroles has been developed. Imines formed in situ via condensation underwent cation-directed cyclization with complete N-regioselectivity. The cyclized products were obtained with enantiomeric ratios up to 96:4 for aldimine substrates and up to 99:1 for trifluoromethyl ketimines. The reaction proceeds without an acidifying group on the pyrrole and offers a new approach to the generation of chiral nonracemic aminals.

Supporting Information