M. Shi, Yukihiro Satoh, Takechi Makihara
Sep 1, 1995
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0
Influential Citations
27
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract Two kinds of chiral C 2 -symmetric 2,5-disubstituted pyrrolidine derivatives having a β-aminoalcohol moiety were successfully synthesized and their catalytic abilities of asymmetric induction were examined in the reaction of diethylzinc with arylaldehydes. The production of sec -alcohols in high yields and high enantiomeric excesses having the R-configuration could be achieved when N-(2′,2′-diphenyl-2′-hydroxyethyl)-(2R, 5R)-bis(methoxymethyl)pyrrolidine was used as a chiral ligand. On the other hand, when N-methyl-(2R, 5R)-bis(diarylhydroxymethyl)pyrrolidine was used as a catalyst, the enantiomeric excesses of the sec -alcohols went down and the inversion of the enantioselectivity was observed in the reaction of m-chloro-, p-chloro-, and m-fluorobenzaldehyde with diethylzinc.