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

doi:10.1016/S1872-2067(14)60317-X

催化学报 ›› 2015, Vol. 36 ›› Issue (7): 1093-1100.DOI: 10.1016/S1872-2067(14)60317-X

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

P. B. Thorat, S. V. Goswami, V. P. Sondankar, S. R. Bhusare

Department of Chemistry, Dnyanopasak College, Parbhani-431401, MS, India

收稿日期:2015-01-05 修回日期:2015-02-10 出版日期:2015-06-12 发布日期:2015-07-30
通讯作者: S. R. Bhusare Tel: +91-2452-242411; Fax: +91-2452-242493; E-mail: bhusare71@yahoo.com

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

P. B. Thorat, S. V. Goswami, V. P. Sondankar, S. R. Bhusare

Department of Chemistry, Dnyanopasak College, Parbhani-431401, MS, India

Received:2015-01-05 Revised:2015-02-10 Online:2015-06-12 Published:2015-07-30

摘要/Abstract

摘要：

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.

关键词: Aldol reaction, Asymmetric synthesis, Chloroacetone, Diastereoselectivity, Hydroxy propanoate, Knoevenagel reaction, Pyrrolidine derivative

Abstract:

Key words: Aldol reaction, Asymmetric synthesis, Chloroacetone, Diastereoselectivity, Hydroxy propanoate, Knoevenagel reaction, Pyrrolidine derivative

P. B. Thorat, S. V. Goswami, V. P. Sondankar, S. R. Bhusare. Stereoselective synthesis of vic-halohydrins and an unusual Knoevenagel product from an organocatalyzed aldol reaction: A non-enamine mode[J]. 催化学报, 2015, 36(7): 1093-1100.

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

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

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