Efficient synthesis of (R)- and (S)-1-amino-2,2-difluorocyclopropanecarboxylic acid via lipase-catalyzed desymmetrization of prochiral precursors

Masayuki Kirihara; Masashi Kawasaki; Tomofumi Takuwa; Hiroko Kakuda; Takahiro Wakikawa; Yoshio Takeuchi; Kenneth L. Kirk

doi:10.1016/S0957-4166(03)00350-1

Efficient synthesis of (R)- and (S)-1-amino-2,2-difluorocyclopropanecarboxylic acid via lipase-catalyzed desymmetrization of prochiral precursors

Masayuki Kirihara^*, Masashi Kawasaki, Tomofumi Takuwa, Hiroko Kakuda, Takahiro Wakikawa, Yoshio Takeuchi, Kenneth L. Kirk

^*Corresponding author for this work

Faculty of Liberal Arts and Sciences

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

41 Scopus citations

Abstract

The asymmetric syntheses of (+)-(R)-1-amino-2,2-difluorocyclopropane-1-carboxylic acid and its enantiomer have been accomplished. Key reactions in the synthetic design are lipase-catalyzed desymmetrization of a prochiral diol and a prochiral diacetate.

Original language	English
Pages (from-to)	1753-1761
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	12
DOIs	https://doi.org/10.1016/S0957-4166(03)00350-1
State	Published - 2003/06/20

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/S0957-4166(03)00350-1

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title = "Efficient synthesis of (R)- and (S)-1-amino-2,2-difluorocyclopropanecarboxylic acid via lipase-catalyzed desymmetrization of prochiral precursors",

abstract = "The asymmetric syntheses of (+)-(R)-1-amino-2,2-difluorocyclopropane-1-carboxylic acid and its enantiomer have been accomplished. Key reactions in the synthetic design are lipase-catalyzed desymmetrization of a prochiral diol and a prochiral diacetate.",

author = "Masayuki Kirihara and Masashi Kawasaki and Tomofumi Takuwa and Hiroko Kakuda and Takahiro Wakikawa and Yoshio Takeuchi and Kirk, {Kenneth L.}",

year = "2003",

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language = "英語",

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T1 - Efficient synthesis of (R)- and (S)-1-amino-2,2-difluorocyclopropanecarboxylic acid via lipase-catalyzed desymmetrization of prochiral precursors

AU - Kirihara, Masayuki

AU - Kawasaki, Masashi

AU - Takuwa, Tomofumi

AU - Kakuda, Hiroko

AU - Wakikawa, Takahiro

AU - Takeuchi, Yoshio

AU - Kirk, Kenneth L.

PY - 2003/6/20

Y1 - 2003/6/20

N2 - The asymmetric syntheses of (+)-(R)-1-amino-2,2-difluorocyclopropane-1-carboxylic acid and its enantiomer have been accomplished. Key reactions in the synthetic design are lipase-catalyzed desymmetrization of a prochiral diol and a prochiral diacetate.

AB - The asymmetric syntheses of (+)-(R)-1-amino-2,2-difluorocyclopropane-1-carboxylic acid and its enantiomer have been accomplished. Key reactions in the synthetic design are lipase-catalyzed desymmetrization of a prochiral diol and a prochiral diacetate.

UR - http://www.scopus.com/inward/record.url?scp=0038205325&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(03)00350-1

DO - 10.1016/S0957-4166(03)00350-1

M3 - 学術論文

AN - SCOPUS:0038205325

SN - 0957-4166

VL - 14

SP - 1753

EP - 1761

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 12

ER -

Efficient synthesis of (R)- and (S)-1-amino-2,2-difluorocyclopropanecarboxylic acid via lipase-catalyzed desymmetrization of prochiral precursors

Abstract

ASJC Scopus subject areas

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