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

6 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 - 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.",

keywords = "1 3-Diol, Chiral DMAP derivative, Desymmetrization",

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

note = "Funding Information: This research was partially supported by a Grant-in-Aid for Young Scientists (B) (17K17903) from JSPS, the JGC-S Scholarship Foundation, Okayama Foundation for Science and Technology, and a Grant-in-Aid for Scientific Research on Innovative Area “Middle Molecular Strategy” from MEXT (Japan). The authors thank Mr. Kenko Abe for preliminary experiments. Publisher Copyright: {\textcopyright} 2018 The Chemical Society of Japan.",

year = "2018",

doi = "10.1246/cl.180697",

language = "English",

volume = "47",

pages = "1360--1363",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "11",

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TY - JOUR

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

AU - Mandai, Hiroki

AU - Ashihara, Kosuke

AU - Mitsudo, Koichi

AU - Suga, Seiji

N1 - Funding Information: This research was partially supported by a Grant-in-Aid for Young Scientists (B) (17K17903) from JSPS, the JGC-S Scholarship Foundation, Okayama Foundation for Science and Technology, and a Grant-in-Aid for Scientific Research on Innovative Area “Middle Molecular Strategy” from MEXT (Japan). The authors thank Mr. Kenko Abe for preliminary experiments. Publisher Copyright: © 2018 The Chemical Society of Japan.

PY - 2018

Y1 - 2018

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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U2 - 10.1246/cl.180697

DO - 10.1246/cl.180697

M3 - Article

AN - SCOPUS:85054816995

VL - 47

SP - 1360

EP - 1363

JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

IS - 11

ER -

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

Abstract

Keywords

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