TY - JOUR
T1 - Non-C2-symmetric, chirally economical, and readily tunable linked-binols
T2 - Design and application in a direct catalytic asymmetric mannich-type reaction
AU - Yoshida, Takamasa
AU - Morimoto, Hiroyuki
AU - Kumagai, Naoya
AU - Matsunaga, Shigeki
AU - Shibasaki, Masakatsu
PY - 2005/5/30
Y1 - 2005/5/30
N2 - (Chemical Equation Presented) An achiral unit is shown to be better than a chiral unit in promoting an asymmetric reaction. Non-C2-symmetric linked-binols 1 with one chiral 1,1′-bi-2-naphthol unit and one flexible achiral unit are employed as ligands in direct catalytic asymmetric Mannich-type reactions (see scheme; TON = turnover number). With as little as 0.01 mol% of ligand 1 a and 0.04 mol% of Et2Zn, the reaction proceeded smoothly to give the product in 98% ee.
AB - (Chemical Equation Presented) An achiral unit is shown to be better than a chiral unit in promoting an asymmetric reaction. Non-C2-symmetric linked-binols 1 with one chiral 1,1′-bi-2-naphthol unit and one flexible achiral unit are employed as ligands in direct catalytic asymmetric Mannich-type reactions (see scheme; TON = turnover number). With as little as 0.01 mol% of ligand 1 a and 0.04 mol% of Et2Zn, the reaction proceeded smoothly to give the product in 98% ee.
KW - Amino alcohols
KW - Asymmetric catalysis
KW - Chiral ligands
KW - Mannich reaction
KW - Zinc
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U2 - 10.1002/anie.200500425
DO - 10.1002/anie.200500425
M3 - Article
C2 - 15861441
AN - SCOPUS:20444420552
VL - 44
SP - 3470
EP - 3474
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 22
ER -