A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes.

Abstract:

:Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the γ-amino alcohols are superior to the corresponding β-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, gave the best results (45-88% yields, 44-81% ee) in the addition reactions. To the best of our knowledge, has been noticed as one of the most efficient γ-amino alcohol catalysts based on pyrrolidine framework.

journal_name

Chirality

journal_title

Chirality

authors

Liu CL,Wei CY,Wang SW,Peng YG

doi

10.1002/chir.21017

subject

Has Abstract

pub_date

2011-11-01 00:00:00

pages

921-8

issue

10

eissn

0899-0042

issn

1520-636X

journal_volume

23

pub_type

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