Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

Jun Kikuchi; Yuki Aizawa; Masahiro Terada

doi:10.1039/d0qo00448k

Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

Jun Kikuchi, Yuki Aizawa, Masahiro Terada

SCI - Chemistry

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

Abstract

An enantioselective intermolecular carbonyl-ene reaction and a Friedel-Crafts-type reaction of 1,1,2-trisubstituted and 1,2-disubstituted simple olefins with ethyl glyoxylate were developed using F10BINOL-derived N-sulfonyl phosphoramide as the chiral strong Brønsted acid catalyst. The present reactions feature an atom-economical and environmentally benign approach to the synthesis of enantioenriched allylic and homoallylic alcohols.

Original language	English
Pages (from-to)	1383-1387
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	7
Issue number	11
DOIs	https://doi.org/10.1039/d0qo00448k
Publication status	Published - 2020 Jun 7

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1039/d0qo00448k

Cite this

@article{e56b2f46c99646838b1126d3921060c9,

title = "Chiral strong Br{\o}nsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate",

abstract = "An enantioselective intermolecular carbonyl-ene reaction and a Friedel-Crafts-type reaction of 1,1,2-trisubstituted and 1,2-disubstituted simple olefins with ethyl glyoxylate were developed using F10BINOL-derived N-sulfonyl phosphoramide as the chiral strong Br{\o}nsted acid catalyst. The present reactions feature an atom-economical and environmentally benign approach to the synthesis of enantioenriched allylic and homoallylic alcohols.",

author = "Jun Kikuchi and Yuki Aizawa and Masahiro Terada",

note = "Funding Information: This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand” from the MEXT, Japan (no. JP17H06447). Publisher Copyright: {\textcopyright} 2020 the Partner Organisations.",

year = "2020",

month = jun,

day = "7",

doi = "10.1039/d0qo00448k",

language = "English",

volume = "7",

pages = "1383--1387",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "11",

}

TY - JOUR

T1 - Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

AU - Kikuchi, Jun

AU - Aizawa, Yuki

AU - Terada, Masahiro

N1 - Funding Information: This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand” from the MEXT, Japan (no. JP17H06447). Publisher Copyright: © 2020 the Partner Organisations.

PY - 2020/6/7

Y1 - 2020/6/7

N2 - An enantioselective intermolecular carbonyl-ene reaction and a Friedel-Crafts-type reaction of 1,1,2-trisubstituted and 1,2-disubstituted simple olefins with ethyl glyoxylate were developed using F10BINOL-derived N-sulfonyl phosphoramide as the chiral strong Brønsted acid catalyst. The present reactions feature an atom-economical and environmentally benign approach to the synthesis of enantioenriched allylic and homoallylic alcohols.

AB - An enantioselective intermolecular carbonyl-ene reaction and a Friedel-Crafts-type reaction of 1,1,2-trisubstituted and 1,2-disubstituted simple olefins with ethyl glyoxylate were developed using F10BINOL-derived N-sulfonyl phosphoramide as the chiral strong Brønsted acid catalyst. The present reactions feature an atom-economical and environmentally benign approach to the synthesis of enantioenriched allylic and homoallylic alcohols.

UR - http://www.scopus.com/inward/record.url?scp=85089583833&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85089583833&partnerID=8YFLogxK

U2 - 10.1039/d0qo00448k

DO - 10.1039/d0qo00448k

M3 - Article

AN - SCOPUS:85089583833

VL - 7

SP - 1383

EP - 1387

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 11

ER -

Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this