Catalytic asymmetric hydroxylation of α-alkoxycarbonyl amides with a Pr(OiPr)3/amide-based ligand catalyst

Sho Takechi; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1016/j.tetlet.2010.11.064

Catalytic asymmetric hydroxylation of α-alkoxycarbonyl amides with a Pr(OⁱPr)₃/amide-based ligand catalyst

Sho Takechi, Naoya Kumagai, Masakatsu Shibasaki

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

29 Citations (Scopus)

Abstract

A catalytic asymmetric hydroxylation of N-nonsubstituted α-alkoxycarbonyl amides is described. A new effective catalyst comprising Pr(OⁱPr)₃ and a fluoro-substituted amide-based ligand was identified using oxaziridine as the oxidizing reagent. The catalyst components were in dynamic equilibrium in the reaction mixture, which assembled to form the associated transition state through metal coordination and hydrogen bonding.

Original language	English
Pages (from-to)	2140-2143
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.064
Publication status	Published - 2011 Apr 27
Externally published	Yes

Keywords

Amide-based ligand
Asymmetric catalysis
Asymmetric hydroxylation
Rare earth metal
Tetrasubstituted stereogenic centers

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2010.11.064

Cite this

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title = "Catalytic asymmetric hydroxylation of α-alkoxycarbonyl amides with a Pr(OiPr)3/amide-based ligand catalyst",

abstract = "A catalytic asymmetric hydroxylation of N-nonsubstituted α-alkoxycarbonyl amides is described. A new effective catalyst comprising Pr(OiPr)3 and a fluoro-substituted amide-based ligand was identified using oxaziridine as the oxidizing reagent. The catalyst components were in dynamic equilibrium in the reaction mixture, which assembled to form the associated transition state through metal coordination and hydrogen bonding.",

keywords = "Amide-based ligand, Asymmetric catalysis, Asymmetric hydroxylation, Rare earth metal, Tetrasubstituted stereogenic centers",

author = "Sho Takechi and Naoya Kumagai and Masakatsu Shibasaki",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research (S) from MEXT . Dr. Motoo Shiro at Rigaku Corporation is gratefully acknowledged for technical assistance for X-ray crystallographic analysis of product 4a . ",

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T1 - Catalytic asymmetric hydroxylation of α-alkoxycarbonyl amides with a Pr(OiPr)3/amide-based ligand catalyst

AU - Takechi, Sho

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research (S) from MEXT . Dr. Motoo Shiro at Rigaku Corporation is gratefully acknowledged for technical assistance for X-ray crystallographic analysis of product 4a .

PY - 2011/4/27

Y1 - 2011/4/27

N2 - A catalytic asymmetric hydroxylation of N-nonsubstituted α-alkoxycarbonyl amides is described. A new effective catalyst comprising Pr(OiPr)3 and a fluoro-substituted amide-based ligand was identified using oxaziridine as the oxidizing reagent. The catalyst components were in dynamic equilibrium in the reaction mixture, which assembled to form the associated transition state through metal coordination and hydrogen bonding.

AB - A catalytic asymmetric hydroxylation of N-nonsubstituted α-alkoxycarbonyl amides is described. A new effective catalyst comprising Pr(OiPr)3 and a fluoro-substituted amide-based ligand was identified using oxaziridine as the oxidizing reagent. The catalyst components were in dynamic equilibrium in the reaction mixture, which assembled to form the associated transition state through metal coordination and hydrogen bonding.

KW - Amide-based ligand

KW - Asymmetric catalysis

KW - Asymmetric hydroxylation

KW - Rare earth metal

KW - Tetrasubstituted stereogenic centers

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