Asymmetric one-pot four-component coupling reaction: Synthesis of substituted tetrahydropyrans catalyzed by diphenylprolinol silyl ether

Hayato Ishikawa; Satoshi Sawano; Yusuke Yasui; Yusuke Shibata; Yujiro Hayashi

doi:10.1002/anie.201005386

Asymmetric one-pot four-component coupling reaction: Synthesis of substituted tetrahydropyrans catalyzed by diphenylprolinol silyl ether

Hayato Ishikawa, Satoshi Sawano, Yusuke Yasui, Yusuke Shibata, Yujiro Hayashi

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

66 Citations (Scopus)

Abstract

(Chemical Equation Presented) Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.

Original language	English
Pages (from-to)	3774-3779
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	16
DOIs	https://doi.org/10.1002/anie.201005386
Publication status	Published - 2011 Apr 11
Externally published	Yes

Keywords

Asymmetric synthesis
Domino reactions
Michael addition
Multicomponent reactions
Organocatalysis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201005386

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abstract = "(Chemical Equation Presented) Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.",

keywords = "Asymmetric synthesis, Domino reactions, Michael addition, Multicomponent reactions, Organocatalysis",

author = "Hayato Ishikawa and Satoshi Sawano and Yusuke Yasui and Yusuke Shibata and Yujiro Hayashi",

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doi = "10.1002/anie.201005386",

language = "English",

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T2 - Synthesis of substituted tetrahydropyrans catalyzed by diphenylprolinol silyl ether

AU - Ishikawa, Hayato

AU - Sawano, Satoshi

AU - Yasui, Yusuke

AU - Shibata, Yusuke

AU - Hayashi, Yujiro

PY - 2011/4/11

Y1 - 2011/4/11

N2 - (Chemical Equation Presented) Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.

AB - (Chemical Equation Presented) Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.

KW - Asymmetric synthesis

KW - Domino reactions

KW - Michael addition

KW - Multicomponent reactions

KW - Organocatalysis

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Asymmetric one-pot four-component coupling reaction: Synthesis of substituted tetrahydropyrans catalyzed by diphenylprolinol silyl ether

Abstract

Keywords

ASJC Scopus subject areas

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