Premium
Modular Bifunctional Chiral Thioureas as Versatile Organocatalysts for Highly Enantioselective Aza‐Henry Reaction and Michael Addition
Author(s) -
Li Hua,
Zhang Xu,
Shi Xin,
Ji Nan,
He Wei,
Zhang Shengyong,
Zhang Bangle
Publication year - 2012
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.201200144
Subject(s) - bifunctional , michael reaction , chemistry , enantioselective synthesis , thiourea , organocatalysis , nitroaldol reaction , nitro , organic chemistry , acetylacetone , cinchona , cinchona alkaloids , acetone , addition reaction , catalysis , alkyl
A series of new modular bifunctional chiral thiourea organocatalysts were synthesized from natural Cinchona alkaloids and amino acids, and their performance in the aza‐Henry reaction of nitroalkanes to imines, the Michael addition of acetylacetone to nitroolefins and the Michael addition of acetone to nitroolefins was investigated. Under the mild conditions, the important building blocks β‐nitro amines and γ‐nitro carbonyl compounds could be obtained in good yields (up to 95%) with excellent enantioselectivities (up to 99% ee ) and diastereoselectivity (up to 17:1).