Preparation of chiral isoxazole carbinols via catalytic asymmetric Corey-Bakshi-Shibata reduction

Kevin C. Rider; David J. Burkhart; Chun Li; Andrew R. Mckenzie; Jared K. Nelson; Nicholas R. Natale

doi:10.3998/ark.5550190.0011.809

Preparation of chiral isoxazole carbinols via catalytic asymmetric Corey-Bakshi-Shibata reduction

Kevin C. Rider, David J. Burkhart, Chun Li, Andrew R. Mckenzie, Jared K. Nelson, Nicholas R. Natale

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

7 Scopus citations

Abstract

A diverse set of isoxazoles, with activity in three different disease categories, was reduced asymmetrically from pro-chiral ketones to chiral alcohols using the Corey-Bakshi-Shibata methodology at the α, β, and γ positions relative to the C-5-methyl of the isoxazole. The experiments described provide an easy route to hydroxylated isoxazoles that represent the common CYP-450 3A4 metabolic site.

Original language	English
Pages (from-to)	97-107
Number of pages	11
Journal	Arkivoc
Volume	2010
Issue number	8
DOIs	https://doi.org/10.3998/ark.5550190.0011.809
State	Published - 2010

Keywords

Asymmetric synthesis
Catalysis
Isoxazole
Oxazaborolidine
Reduction

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10.3998/ark.5550190.0011.809

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title = "Preparation of chiral isoxazole carbinols via catalytic asymmetric Corey-Bakshi-Shibata reduction",

abstract = "A diverse set of isoxazoles, with activity in three different disease categories, was reduced asymmetrically from pro-chiral ketones to chiral alcohols using the Corey-Bakshi-Shibata methodology at the α, β, and γ positions relative to the C-5-methyl of the isoxazole. The experiments described provide an easy route to hydroxylated isoxazoles that represent the common CYP-450 3A4 metabolic site.",

keywords = "Asymmetric synthesis, Catalysis, Isoxazole, Oxazaborolidine, Reduction",

author = "Rider, \{Kevin C.\} and Burkhart, \{David J.\} and Chun Li and Mckenzie, \{Andrew R.\} and Nelson, \{Jared K.\} and Natale, \{Nicholas R.\}",

year = "2010",

doi = "10.3998/ark.5550190.0011.809",

language = "English",

volume = "2010",

pages = "97--107",

journal = "Arkivoc",

issn = "1551-7012",

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TY - JOUR

T1 - Preparation of chiral isoxazole carbinols via catalytic asymmetric Corey-Bakshi-Shibata reduction

AU - Rider, Kevin C.

AU - Burkhart, David J.

AU - Li, Chun

AU - Mckenzie, Andrew R.

AU - Nelson, Jared K.

AU - Natale, Nicholas R.

PY - 2010

Y1 - 2010

N2 - A diverse set of isoxazoles, with activity in three different disease categories, was reduced asymmetrically from pro-chiral ketones to chiral alcohols using the Corey-Bakshi-Shibata methodology at the α, β, and γ positions relative to the C-5-methyl of the isoxazole. The experiments described provide an easy route to hydroxylated isoxazoles that represent the common CYP-450 3A4 metabolic site.

AB - A diverse set of isoxazoles, with activity in three different disease categories, was reduced asymmetrically from pro-chiral ketones to chiral alcohols using the Corey-Bakshi-Shibata methodology at the α, β, and γ positions relative to the C-5-methyl of the isoxazole. The experiments described provide an easy route to hydroxylated isoxazoles that represent the common CYP-450 3A4 metabolic site.

KW - Asymmetric synthesis

KW - Catalysis

KW - Isoxazole

KW - Oxazaborolidine

KW - Reduction

UR - https://www.scopus.com/pages/publications/77953469090

U2 - 10.3998/ark.5550190.0011.809

DO - 10.3998/ark.5550190.0011.809

M3 - Article

AN - SCOPUS:77953469090

SN - 1551-7012

VL - 2010

SP - 97

EP - 107

JO - Arkivoc

JF - Arkivoc

IS - 8

ER -

Preparation of chiral isoxazole carbinols via catalytic asymmetric Corey-Bakshi-Shibata reduction

Abstract

Keywords

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