Premium
Enantioselective Organocatalytic Synthesis of 1,2,3‐Trisubstituted Cyclopentanes
Author(s) -
Šotolová Martina,
Kamlar Martin,
Remeš Marek,
Géant PierreYves,
Císařová Ivana,
Štícha Martin,
Veselý Jan
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100841
Subject(s) - cyclopentanes , chemistry , enantioselective synthesis , cyclopentane , organocatalysis , domino , organic chemistry , alkylation , alkyl , amine gas treating , catalysis , halide , cascade reaction , combinatorial chemistry
Abstract An organocatalytic asymmetric domino Michael/α‐alkylation reaction between enals and non‐stabilized alkyl halides has been developed. Chiral secondary amine catalyzed cyclization reaction of 1‐bromo‐3‐nitropropane with α,β‐unsaturated aldehydes provides 1,2,3‐trisubstituted cyclopentane carbaldehydes with high diastereo‐ (dr up to 8 : 1) and enantioselectivities ( ee up to 96 %).