Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative

Hiroki Mandai; Kosuke Ashihara; Koichi Mitsudo; Seiji Suga

doi:10.1246/cl.180697

Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative

Hiroki Mandai, Kosuke Ashihara, Koichi Mitsudo, Seiji Suga

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

3 Citations (Scopus)

Abstract

We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.

Original language	English
Pages (from-to)	1360-1363
Number of pages	4
Journal	Chemistry Letters
Volume	47
Issue number	11
DOIs	https://doi.org/10.1246/cl.180697
Publication status	Published - Jan 1 2018

Keywords

1 3-Diol
Chiral DMAP derivative
Desymmetrization

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.180697

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title = "Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative",

abstract = "We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.",

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T1 - Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative

AU - Mandai, Hiroki

AU - Ashihara, Kosuke

AU - Mitsudo, Koichi

AU - Suga, Seiji

PY - 2018/1/1

Y1 - 2018/1/1

N2 - We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.

AB - We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.

KW - 1 3-Diol

KW - Chiral DMAP derivative

KW - Desymmetrization

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