Highly enantioselective synthesis of β-hydroxysulfonamides by asymmetric transfer hydrogenation

Asymmetric transfer hydrogenation of β-oxosulfonamides using the Ru–TsDPEN–HCOOH–Et 3N catalytic system gives the corresponding optically active β-hydroxysulfonamides in excellent yields (up to 95%) with excellent diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to >99% ee). A...

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Published in:Tetrahedron letters 2011-02, Vol.52 (8), p.907-909
Main Authors: Geng, Zhicong, Wu, Yun, Miao, Shifeng, Shen, Zongxuan, Zhang, Yawen
Format: Article
Language:English
Subjects:
Asymmetry
Catalysis
Catalysts
Hydrogenation
Optical activity
Synthesis (chemistry)
Tetrahedrons
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description Asymmetric transfer hydrogenation of β-oxosulfonamides using the Ru–TsDPEN–HCOOH–Et 3N catalytic system gives the corresponding optically active β-hydroxysulfonamides in excellent yields (up to 95%) with excellent diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to >99% ee). A series of optically active β-hydroxy sulfonamides were synthesized for the first time by asymmetric transfer hydrogenation of the corresponding β-ketosulfonamides using the Ru–TsDPEN–HCOOH–Et 3N catalytic system, in excellent yields (up to 95%) with excellent diastereo- (up to > 99:1 dr) and enantioselectivities (up to >99% ee).
doi_str_mv 10.1016/j.tetlet.2010.12.054
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subjects Asymmetry
Catalysis
Catalysts
Hydrogenation
Optical activity
Synthesis (chemistry)
Tetrahedrons
title Highly enantioselective synthesis of β-hydroxysulfonamides by asymmetric transfer hydrogenation
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