Structurally well-defined, recoverable C3-symmetric tris(β-hydroxy phosphoramide)-catalyzed enantioselective borane reduction of ketones

Da Ming Du; Tao Fang; Jiaxi Xu; Shi Wei Zhang

doi:10.1021/ol0600584

Structurally well-defined, recoverable C₃-symmetric tris(β-hydroxy phosphoramide)-catalyzed enantioselective borane reduction of ketones

Da Ming Du^*, Tao Fang, Jiaxi Xu, Shi Wei Zhang

^*Corresponding author for this work

Peking University

Research output: Contribution to journal › Article › peer-review

61 Citations (Scopus)

Abstract

A series of new chiral C₃-symmetric tris(β-hydroxy phosphoramide) ligands have been synthesized via the reaction of trisphosphoramide ester and Grignard reagents. The catalytic asymmetric borane reduction of ketones with these new C₃-symmetric chiral tris(β-hydroxy phosphoramide)s was investigated. Structurally well-defined, recoverable ligand 1d is an efficient catalyst for the enantioselective borane reduction of both electron-deficient and electron-rich ketones, and high enantioselectivities were achieved (up to 98% ee).

Original language	English
Pages (from-to)	1327-1330
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	7
DOIs	https://doi.org/10.1021/ol0600584
Publication status	Published - 30 Mar 2006
Externally published	Yes

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Du, D. M., Fang, T., Xu, J., & Zhang, S. W. (2006). Structurally well-defined, recoverable C₃-symmetric tris(β-hydroxy phosphoramide)-catalyzed enantioselective borane reduction of ketones. Organic Letters, 8(7), 1327-1330. https://doi.org/10.1021/ol0600584

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abstract = "A series of new chiral C3-symmetric tris(β-hydroxy phosphoramide) ligands have been synthesized via the reaction of trisphosphoramide ester and Grignard reagents. The catalytic asymmetric borane reduction of ketones with these new C3-symmetric chiral tris(β-hydroxy phosphoramide)s was investigated. Structurally well-defined, recoverable ligand 1d is an efficient catalyst for the enantioselective borane reduction of both electron-deficient and electron-rich ketones, and high enantioselectivities were achieved (up to 98% ee).",

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AU - Du, Da Ming

AU - Fang, Tao

AU - Xu, Jiaxi

AU - Zhang, Shi Wei

PY - 2006/3/30

Y1 - 2006/3/30

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AB - A series of new chiral C3-symmetric tris(β-hydroxy phosphoramide) ligands have been synthesized via the reaction of trisphosphoramide ester and Grignard reagents. The catalytic asymmetric borane reduction of ketones with these new C3-symmetric chiral tris(β-hydroxy phosphoramide)s was investigated. Structurally well-defined, recoverable ligand 1d is an efficient catalyst for the enantioselective borane reduction of both electron-deficient and electron-rich ketones, and high enantioselectivities were achieved (up to 98% ee).

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Structurally well-defined, recoverable C₃-symmetric tris(β-hydroxy phosphoramide)-catalyzed enantioselective borane reduction of ketones

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