Enantioselective Organocatalytic Construction of Spirochroman Derivatives

Keisuke Yoshida; Hiroki Inoue; Yurika Oji; Hina Suzuki; Ken Ichi Takao

doi:10.1021/acs.joc.0c00589

Enantioselective Organocatalytic Construction of Spirochroman Derivatives

Keisuke Yoshida, Hiroki Inoue, Yurika Oji, Hina Suzuki, Ken Ichi Takao

Department of Applied Chemistry

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

7 Citations (Scopus)

Abstract

Highly enantioselective organocatalytic construction of spirochromans containing a tetrasubstituted stereocenter was developed. Intramolecular oxy-Michael addition was catalyzed with a bifunctional cinchona alkaloid thiourea catalyst. A variety of spirochroman compounds containing a tetrasubstituted stereocenter were obtained with excellent enantioselectivities of up to 99% enantiomeric excess. The reaction was applied to the asymmetric formal synthesis of (-)-(R)-cordiachromene.

Original language	English
Pages (from-to)	10189-10197
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	85
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.0c00589
Publication status	Published - 2020 Aug 7

ASJC Scopus subject areas

Organic Chemistry

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title = "Enantioselective Organocatalytic Construction of Spirochroman Derivatives",

abstract = "Highly enantioselective organocatalytic construction of spirochromans containing a tetrasubstituted stereocenter was developed. Intramolecular oxy-Michael addition was catalyzed with a bifunctional cinchona alkaloid thiourea catalyst. A variety of spirochroman compounds containing a tetrasubstituted stereocenter were obtained with excellent enantioselectivities of up to 99% enantiomeric excess. The reaction was applied to the asymmetric formal synthesis of (-)-(R)-cordiachromene.",

author = "Keisuke Yoshida and Hiroki Inoue and Yurika Oji and Hina Suzuki and Takao, {Ken Ichi}",

note = "Funding Information: This research was supported by JSPS KAKENHI Grant Number 16K17903. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

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AU - Yoshida, Keisuke

AU - Inoue, Hiroki

AU - Oji, Yurika

AU - Suzuki, Hina

AU - Takao, Ken Ichi

N1 - Funding Information: This research was supported by JSPS KAKENHI Grant Number 16K17903. Publisher Copyright: Copyright © 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/8/7

Y1 - 2020/8/7

N2 - Highly enantioselective organocatalytic construction of spirochromans containing a tetrasubstituted stereocenter was developed. Intramolecular oxy-Michael addition was catalyzed with a bifunctional cinchona alkaloid thiourea catalyst. A variety of spirochroman compounds containing a tetrasubstituted stereocenter were obtained with excellent enantioselectivities of up to 99% enantiomeric excess. The reaction was applied to the asymmetric formal synthesis of (-)-(R)-cordiachromene.

AB - Highly enantioselective organocatalytic construction of spirochromans containing a tetrasubstituted stereocenter was developed. Intramolecular oxy-Michael addition was catalyzed with a bifunctional cinchona alkaloid thiourea catalyst. A variety of spirochroman compounds containing a tetrasubstituted stereocenter were obtained with excellent enantioselectivities of up to 99% enantiomeric excess. The reaction was applied to the asymmetric formal synthesis of (-)-(R)-cordiachromene.

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Enantioselective Organocatalytic Construction of Spirochroman Derivatives

Abstract

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