Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives

Hiroki Mandai; Kosuke Ashihara; Koichi Mitsudo; Seiji Suga

doi:10.3987/COM-21-14433

Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives

Hiroki Mandai, Kosuke Ashihara, Koichi Mitsudo, Seiji Suga

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

1 Citation (Scopus)

Abstract

An efficient enantioselective acylative desymmetrization of glycerol was developed by using a chiral DMAP derivatives 1e having a 1,1-binaphthyl unit. The reactions required only 0.1 mol% of the catalyst and showed moderate to good enantioselectivity (up to 94:6 er). Control experiments revealed that the first acylation of a glycerol derivative proceeded selectively rather than the second acylation to give diacylate.

Original language	English
Pages (from-to)	1083-1090
Number of pages	8
Journal	Heterocycles
Volume	102
Issue number	6
DOIs	https://doi.org/10.3987/COM-21-14433
Publication status	Published - 2021

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-21-14433

Cite this

@article{146c02e585a4458099e75dec2d65f88a,

title = "Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives",

abstract = "An efficient enantioselective acylative desymmetrization of glycerol was developed by using a chiral DMAP derivatives 1e having a 1,1-binaphthyl unit. The reactions required only 0.1 mol% of the catalyst and showed moderate to good enantioselectivity (up to 94:6 er). Control experiments revealed that the first acylation of a glycerol derivative proceeded selectively rather than the second acylation to give diacylate.",

author = "Hiroki Mandai and Kosuke Ashihara and Koichi Mitsudo and Seiji Suga",

note = "Funding Information: This research was partially supported by the Japan Soap and Detergent Association (JSDA) and JSPS Kakenhi Grant Number JP19K05456. Publisher Copyright: {\textcopyright} 2021 The Japan Institute of Heterocyclic Chemistry",

year = "2021",

doi = "10.3987/COM-21-14433",

language = "English",

volume = "102",

pages = "1083--1090",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "6",

}

TY - JOUR

T1 - Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives

AU - Mandai, Hiroki

AU - Ashihara, Kosuke

AU - Mitsudo, Koichi

AU - Suga, Seiji

N1 - Funding Information: This research was partially supported by the Japan Soap and Detergent Association (JSDA) and JSPS Kakenhi Grant Number JP19K05456. Publisher Copyright: © 2021 The Japan Institute of Heterocyclic Chemistry

PY - 2021

Y1 - 2021

N2 - An efficient enantioselective acylative desymmetrization of glycerol was developed by using a chiral DMAP derivatives 1e having a 1,1-binaphthyl unit. The reactions required only 0.1 mol% of the catalyst and showed moderate to good enantioselectivity (up to 94:6 er). Control experiments revealed that the first acylation of a glycerol derivative proceeded selectively rather than the second acylation to give diacylate.

AB - An efficient enantioselective acylative desymmetrization of glycerol was developed by using a chiral DMAP derivatives 1e having a 1,1-binaphthyl unit. The reactions required only 0.1 mol% of the catalyst and showed moderate to good enantioselectivity (up to 94:6 er). Control experiments revealed that the first acylation of a glycerol derivative proceeded selectively rather than the second acylation to give diacylate.

UR - http://www.scopus.com/inward/record.url?scp=85107910078&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85107910078&partnerID=8YFLogxK

U2 - 10.3987/COM-21-14433

DO - 10.3987/COM-21-14433

M3 - Article

AN - SCOPUS:85107910078

SN - 0385-5414

VL - 102

SP - 1083

EP - 1090

JO - Heterocycles

JF - Heterocycles

IS - 6

ER -

Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this