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

63 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)

Access to Document

10.1002/anie.201005386

Cite this

Asymmetric one-pot four-component coupling reaction : Synthesis of substituted tetrahydropyrans catalyzed by diphenylprolinol silyl ether. / Ishikawa, Hayato; Sawano, Satoshi; Yasui, Yusuke; Shibata, Yusuke; Hayashi, Yujiro.

In: Angewandte Chemie - International Edition, Vol. 50, No. 16, 11.04.2011, p. 3774-3779.

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

@article{ea4842c96efb41c6a0c5b32201c81fd6,

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

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",

year = "2011",

month = apr,

day = "11",

doi = "10.1002/anie.201005386",

language = "English",

volume = "50",

pages = "3774--3779",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "16",

}

TY - JOUR

T1 - Asymmetric one-pot four-component coupling reaction

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

UR - http://www.scopus.com/inward/record.url?scp=79953709139&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79953709139&partnerID=8YFLogxK

U2 - 10.1002/anie.201005386

DO - 10.1002/anie.201005386

M3 - Article

C2 - 21438102

AN - SCOPUS:79953709139

VL - 50

SP - 3774

EP - 3779

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 16

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this