Stereoselective synthesis of vic-halohydrins and an unusual Knoevenagel product from an organocatalyzed aldol reaction: A non-enamine mode

Stereoselective synthesis by an aldol reaction between chloroacetone and aldehyde was studied using a synthesized chiral organocatalyst and triethylamine. The reaction gave α-chloro-β-hydroxy ketones in excellent yield with high anti selectivity and enantioselectivity. The chiral organocatalyst was...

Full description

Saved in:
Bibliographic Details
Published in:Chinese journal of catalysis 2015-07, Vol.36 (7), p.1093-1100
Main Authors: Thorat, P.B., Goswami, S.V., Sondankar, V.P., Bhusare, S.R.
Format: Article
Language:English
Subjects:
Aldol reaction
Asymmetric synthesis
Chloroacetone
Diastereoselectivity
Hydroxy propanoate
Knoevenagel reaction
Pyrrolidine derivative
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Stereoselective synthesis by an aldol reaction between chloroacetone and aldehyde was studied using a synthesized chiral organocatalyst and triethylamine. The reaction gave α-chloro-β-hydroxy ketones in excellent yield with high anti selectivity and enantioselectivity. The chiral organocatalyst was also used in the Knoevenagel reaction, which gave α-cyano-β-hydroxy ketones at a low temperature and the usual Knoevenagel product at a high temperature. Both products were obtained in good to moderate yield with good anti selectivity in the case of α-cyano-β-hydroxy ketone derivatives. Stereoselective synthesis of vic-halohydrins and an unusual Knoevenagel product were obtained using a newly synthesized chiral organocatalyst and triethylamine. The reaction gave the products in excellent yield with high anti selectivity and enantioselectivity.
ISSN:1872-2067
1872-2067
DOI:10.1016/S1872-2067(14)60317-X