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- W2079382443 abstract "Chiral C2-symmetric 2,3-disubstituted aziridines and 2,6-disubstituted piperidines having a β-amino alcohol moiety have been successfully synthesized and their catalytic chiral induction properties have been examined in the asymmetric addition reactions of diethylzinc with arylaldehydes in hexane. When N-(2,2-diphenyl-2-hydroxyethyl)-(S,S)-2,3-bis(methoxymethyl)aziridine 11 was used as a catalytic chiral ligand, sec-alcohols having (S)-configuration formed in high yields of 86–92% but low enantiomeric excesses (ee's) of 11–13%. However, when N-(2,2-diphenyl-2-hydroxyethyl)-(R,R)-2,6-disubstituted piperidine derivatives 16 and 20 were used as the chiral ligands under the same reaction conditions, the ee's of the corresponding sec-alcohols were 20–30 and 5–6%, respectively, along with the inversion of absolute configuration. A plausible mechanism for this inversion is proposed." @default.
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- W2079382443 date "2000-12-01" @default.
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- W2079382443 title "Chiral C 2 -symmetric 2,3-disubstituted aziridine and 2,6-disubstituted piperidine as chiral ligands in the addition reaction of diethylzinc with arylaldehydes" @default.
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- W2079382443 doi "https://doi.org/10.1016/s0957-4166(00)00479-1" @default.
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