Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Brønsted base

Azusa Kondoh; Hoa Thi Quynh Tran; Kyoko Kimura; Masahiro Terada

doi:10.1039/c6cc01690a

Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Brønsted base

Azusa Kondoh, Hoa Thi Quynh Tran, Kyoko Kimura, Masahiro Terada

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

16 Citations (Scopus)

Abstract

An enantioselective intramolecular cyclization reaction of alkynyl esters was developed, which employs a Brønsted base catalyst generated in situ from a chiral Schiff base and t-BuOK. This reaction is a rare example of the enantioselective intramolecular addition of simple ester enolates to alkynes under Brønsted base catalysis.

Original language	English
Pages (from-to)	5726-5729
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	33
DOIs	https://doi.org/10.1039/c6cc01690a
Publication status	Published - 2016 Apr 28

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Br{\o}nsted base",

abstract = "An enantioselective intramolecular cyclization reaction of alkynyl esters was developed, which employs a Br{\o}nsted base catalyst generated in situ from a chiral Schiff base and t-BuOK. This reaction is a rare example of the enantioselective intramolecular addition of simple ester enolates to alkynes under Br{\o}nsted base catalysis.",

author = "Azusa Kondoh and Tran, {Hoa Thi Quynh} and Kyoko Kimura and Masahiro Terada",

note = "Funding Information: This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas {"}Advanced Molecular Transformations by Organocatalysts{"} from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, and a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

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doi = "10.1039/c6cc01690a",

language = "English",

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T1 - Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Brønsted base

AU - Kondoh, Azusa

AU - Tran, Hoa Thi Quynh

AU - Kimura, Kyoko

AU - Terada, Masahiro

N1 - Funding Information: This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas "Advanced Molecular Transformations by Organocatalysts" from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, and a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016/4/28

Y1 - 2016/4/28

N2 - An enantioselective intramolecular cyclization reaction of alkynyl esters was developed, which employs a Brønsted base catalyst generated in situ from a chiral Schiff base and t-BuOK. This reaction is a rare example of the enantioselective intramolecular addition of simple ester enolates to alkynes under Brønsted base catalysis.

AB - An enantioselective intramolecular cyclization reaction of alkynyl esters was developed, which employs a Brønsted base catalyst generated in situ from a chiral Schiff base and t-BuOK. This reaction is a rare example of the enantioselective intramolecular addition of simple ester enolates to alkynes under Brønsted base catalysis.

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JF - Chemical Communications

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Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Brønsted base

Abstract

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