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Angew Chem Int Ed Engl. 2018 Oct 8;57(41):13547-13550. doi: 10.1002/anie.201808392. Epub 2018 Sep 17.

Catalytic Regio- and Enantioselective Alkylation of Conjugated Dienyl Amides.

Author information

1
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

Abstract

A method for catalytic asymmetric alkylation of conjugated dienyl amides has been developed and it allows efficient and high-yielding transformations of a wide range of polyconjugated amides into the corresponding chiral products. Smooth addition of organomagnesium reagents to relatively unreactive dienyl amides with excellent 1,6- and 1,4-selectivities, as well as enantioselectivites above 90‚ÄČ%, is achieved owing to the complementary action of the Lewis acid and a chiral copper-based catalyst.

KEYWORDS:

Lewis acids; asymmetric catalysis; conjugation; copper; regioselectivity

PMID:
30144263
DOI:
10.1002/anie.201808392

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