TY - JOUR
T1 - Cooperative asymmetric catalysis using thioamides toward truly practical organic syntheses
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
PY - 2012/7
Y1 - 2012/7
N2 - Asymmetric catalysis has established its unwavering position in organic chemistry as a particularly efficient strategy for the production of enantiomerically enriched compounds. For a truly practical synthetic protocol, however, asymmetric catalysis must be endowed with high atom economy and sustainability. Cooperative activation is a powerful strategy to drive efficient asymmetric catalysis without the use of stoichiometric activating reagents, leading to asymmetric catalysis with minimum waste production. This review summarizes the utility of thioamides as an emerging functional group class in cooperative asymmetric catalysis. Soft Lewis acid/hard Brønsted base cooperative catalysts, in which thioamides serve as either electrophiles or pronucleophiles, promote asymmetric C-C bond-forming reactions with perfect atom economy.
AB - Asymmetric catalysis has established its unwavering position in organic chemistry as a particularly efficient strategy for the production of enantiomerically enriched compounds. For a truly practical synthetic protocol, however, asymmetric catalysis must be endowed with high atom economy and sustainability. Cooperative activation is a powerful strategy to drive efficient asymmetric catalysis without the use of stoichiometric activating reagents, leading to asymmetric catalysis with minimum waste production. This review summarizes the utility of thioamides as an emerging functional group class in cooperative asymmetric catalysis. Soft Lewis acid/hard Brønsted base cooperative catalysts, in which thioamides serve as either electrophiles or pronucleophiles, promote asymmetric C-C bond-forming reactions with perfect atom economy.
KW - asymmetric catalysis
KW - atom economy
KW - cooperative catalysis
KW - proton transfer conditions
KW - thioamide
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U2 - 10.1002/ijch.201100164
DO - 10.1002/ijch.201100164
M3 - Review article
AN - SCOPUS:84864201362
VL - 52
SP - 604
EP - 612
JO - Israel Journal of Chemistry
JF - Israel Journal of Chemistry
SN - 0021-2148
IS - 7
ER -