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

Abstract

Abstract:

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.

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]. Chinese Journal of Catalysis, 2015, 36(7): 1093-1100.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60317-X

https://www.cjcatal.com/EN/Y2015/V36/I7/1093

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