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Asymmetric Aldol Reaction of Pyruvate Promoted by Chiral Tertiary Amines
Author(s) -
PasternakSuder Monika,
Pacułt Wojciech,
Baś Sebastian,
Mlynarski Jacek
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001450
Subject(s) - aldol reaction , chemistry , moiety , aldol condensation , aldehyde , enantioselective synthesis , phenol , selectivity , organic chemistry , tertiary amine , catalysis , combinatorial chemistry
The direct asymmetric aldol reaction of α‐ketoesters catalyzed by chiral tertiary amines is reported. The described methodology is characterized by mild reaction conditions and distinct product selectivity determined by the starting materials. In the developed transformation pyruvates undergo highly selective self‐condensation reaction, whereas cross‐aldol reaction take place predominantly for their carbon chain homologues in presence of aldehyde acceptors. Notably, addition of bulky phenol moiety into pyruvate inhibit the spontaneous lactonization of products and enhance the enantioselectivity.