Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester

Masayuki Sakuma; Akira Sakakura; Kazuaki Ishihara

doi:10.1021/ol401313d

Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester

Masayuki Sakuma, Akira Sakakura, Kazuaki Ishihara

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

35 Citations (Scopus)

Abstract

Chiral phosphonium salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S (= k_fast/k _slow) values. Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. Notably, chiral phosphonous acid diester not only induced the enantioselectivity but also promoted protolactonization.

Original language	English
Pages (from-to)	2838-2841
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	11
DOIs	https://doi.org/10.1021/ol401313d
Publication status	Published - Jun 7 2013

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol401313d

Cite this

@article{5037b913faca47858533c1cf1c9550f4,

title = "Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester",

abstract = "Chiral phosphonium salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S (= kfast/k slow) values. Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. Notably, chiral phosphonous acid diester not only induced the enantioselectivity but also promoted protolactonization.",

author = "Masayuki Sakuma and Akira Sakakura and Kazuaki Ishihara",

year = "2013",

month = jun,

day = "7",

doi = "10.1021/ol401313d",

language = "English",

volume = "15",

pages = "2838--2841",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester

AU - Sakuma, Masayuki

AU - Sakakura, Akira

AU - Ishihara, Kazuaki

PY - 2013/6/7

Y1 - 2013/6/7

N2 - Chiral phosphonium salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S (= kfast/k slow) values. Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. Notably, chiral phosphonous acid diester not only induced the enantioselectivity but also promoted protolactonization.

AB - Chiral phosphonium salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S (= kfast/k slow) values. Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. Notably, chiral phosphonous acid diester not only induced the enantioselectivity but also promoted protolactonization.

UR - http://www.scopus.com/inward/record.url?scp=84879218764&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84879218764&partnerID=8YFLogxK

U2 - 10.1021/ol401313d

DO - 10.1021/ol401313d

M3 - Article

C2 - 23676002

AN - SCOPUS:84879218764

SN - 1523-7060

VL - 15

SP - 2838

EP - 2841

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this