Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chirally Modified AZADOs

Masaki Tomizawa; Masatoshi Shibuya; Yoshiharu Iwabuchi

doi:10.1021/ol900441f

Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chirally Modified AZADOs

Masaki Tomizawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

Tohoku University

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

63 Citations (Scopus)

Abstract

A highly enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols has been accomplished using asymmetric organocatalysis. A panel of chirally modified 2-azaadamantane N-oxyls (AZADOs) exhibit superior catalytic activity and high enantioselectivity, allowing us to obtain optically active secondary alcohols with a k_rel value up to 82.2.

Original language	English
Pages (from-to)	1828-1831
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	8
DOIs	https://doi.org/10.1021/ol900441f
Publication status	Published - 2009 Apr 16

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abstract = "A highly enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols has been accomplished using asymmetric organocatalysis. A panel of chirally modified 2-azaadamantane N-oxyls (AZADOs) exhibit superior catalytic activity and high enantioselectivity, allowing us to obtain optically active secondary alcohols with a krel value up to 82.2.",

author = "Masaki Tomizawa and Masatoshi Shibuya and Yoshiharu Iwabuchi",

year = "2009",

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T1 - Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chirally Modified AZADOs

AU - Tomizawa, Masaki

AU - Shibuya, Masatoshi

AU - Iwabuchi, Yoshiharu

PY - 2009/4/16

Y1 - 2009/4/16

N2 - A highly enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols has been accomplished using asymmetric organocatalysis. A panel of chirally modified 2-azaadamantane N-oxyls (AZADOs) exhibit superior catalytic activity and high enantioselectivity, allowing us to obtain optically active secondary alcohols with a krel value up to 82.2.

AB - A highly enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols has been accomplished using asymmetric organocatalysis. A panel of chirally modified 2-azaadamantane N-oxyls (AZADOs) exhibit superior catalytic activity and high enantioselectivity, allowing us to obtain optically active secondary alcohols with a krel value up to 82.2.

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chirally Modified AZADOs

Abstract

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