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Amine Catalysis with Substrates Bearing N ‐Heterocyclic Moieties Enabled by Control over the Enamine Pyramidalization Direction
Author(s) -
Möhler Jasper S.,
Schnitzer Tobias,
Wennemers Helma
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002966
Subject(s) - enamine , stereoselectivity , chemistry , catalysis , amine gas treating , conjugate , combinatorial chemistry , organocatalysis , stereochemistry , organic chemistry , enantioselective synthesis , mathematical analysis , mathematics
Stereoselective organocatalytic C−C bond formations that tolerate N ‐heterocycles are valuable since these moieties are common motifs in numerous chiral bioactive compounds. Such transformations are, however, challenging since N ‐heterocyclic moieties can interfere with the catalytic reaction. Here, we present a peptide that catalyzes conjugate addition reactions between aldehydes and nitroolefins bearing a broad range of different N ‐heterocyclic moieties with basic and/or H‐bonding sites in excellent yields and stereoselectivities. Tuning of the pyramidalization direction of the enamine intermediate enabled the high stereoselectivity.