TY - JOUR
T1 - Catalytic asymmetric phase-transfer michael reaction and Mannich-type reaction of glycine schiff bases with tartrate-derived diammonium salts
AU - Shibuguchi, Tomoyuki
AU - Mihara, Hisashi
AU - Kuramochi, Akiyoshi
AU - Ohshima, Takashi
AU - Shibasaki, Masakatsu
PY - 2007
Y1 - 2007
N2 - Catalytic asymmetric Michael and Mannich-type reactions of glycine Schiff hases with chiral two-center organocatalysts, tartrate-derived diammonium salts (TaDiASs), are described. On the basis of conformational studies, optimized TaDiASs with a 2,6-disubstituted cyclohexane spiroacetal were newly designed. These TaDiASs catalyzed the asymmetric Michael and Mannich-type reactions of glycine Schiff bases with higher enantioselectivity than previous catalysts. In the Mannich-type reaction, aromatic N- Boc-protected imines (Boc = tert-butoxycarbonyl) as well as enolizable alkyl imines were applicable. As a synthetic application of the catalytic asymmetric Mannich-type reaction with the optimized TaDiASs. we developed a catalytic asymmetric total synthesis of (+)-nemonapride, which is an antipsychotic agent.
AB - Catalytic asymmetric Michael and Mannich-type reactions of glycine Schiff hases with chiral two-center organocatalysts, tartrate-derived diammonium salts (TaDiASs), are described. On the basis of conformational studies, optimized TaDiASs with a 2,6-disubstituted cyclohexane spiroacetal were newly designed. These TaDiASs catalyzed the asymmetric Michael and Mannich-type reactions of glycine Schiff bases with higher enantioselectivity than previous catalysts. In the Mannich-type reaction, aromatic N- Boc-protected imines (Boc = tert-butoxycarbonyl) as well as enolizable alkyl imines were applicable. As a synthetic application of the catalytic asymmetric Mannich-type reaction with the optimized TaDiASs. we developed a catalytic asymmetric total synthesis of (+)-nemonapride, which is an antipsychotic agent.
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U2 - 10.1002/asia.200700070
DO - 10.1002/asia.200700070
M3 - Review article
C2 - 17492797
AN - SCOPUS:34250625513
VL - 2
SP - 794
EP - 801
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 6
ER -