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Organocatalyzed Deracemization of Δ 2 ‐Pyrrolin‐4‐ones
Author(s) -
Ričko Sebastijan,
Meden Anže,
Ivančič Anže,
Perdih Andrej,
Štefane Bogdan,
Svete Jurij,
Grošelj Uroš
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700539
Subject(s) - chemistry , bifunctional , organocatalysis , substrate (aquarium) , stereoselectivity , enantioselective synthesis , diamine , scope (computer science) , camphor , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , programming language , oceanography , geology , computer science
Racemic pyrrolin‐4‐ones, accessible from α ‐amino acids, undergo asymmetric stereoselective organocatalyzed 1,4‐additions to trans ‐β‐nitrostyrenes (up to 98 % ee ; dr up to 97:3). From a series of typical organocatalysts, the best performance was achieved using (+)‐camphor‐1,3‐diamine‐derived bifunctional organocatalysts. A broad substrate scope and some follow‐up modifications have been demonstrated.