Asymmetric diels-alder reactions of α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water

Yujiro Hayashi; Sampak Samanta; Hiroaki Gotoh; Hayato Ishikawa

doi:10.1002/anie.200801408

Asymmetric diels-alder reactions of α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water

Yujiro Hayashi, Sampak Samanta, Hiroaki Gotoh, Hayato Ishikawa

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

141 Citations (Scopus)

Abstract

(Chemical Equation Presented) Water, water, everywhere: The title reaction predominantly affords the exo isomer with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). The synthesis can be carried out without organic solvents and provides the products by distillation. Water increases the rate and enantioselectivity of the reaction.

Original language	English
Pages (from-to)	6634-6637
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	35
DOIs	https://doi.org/10.1002/anie.200801408
Publication status	Published - 2008 Aug 18
Externally published	Yes

Keywords

Asymmetric synthesis
Cycloaddition
Enantioselectivity
Organocatalysis
Water chemistry

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200801408

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abstract = "(Chemical Equation Presented) Water, water, everywhere: The title reaction predominantly affords the exo isomer with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). The synthesis can be carried out without organic solvents and provides the products by distillation. Water increases the rate and enantioselectivity of the reaction.",

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author = "Yujiro Hayashi and Sampak Samanta and Hiroaki Gotoh and Hayato Ishikawa",

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AU - Hayashi, Yujiro

AU - Samanta, Sampak

AU - Gotoh, Hiroaki

AU - Ishikawa, Hayato

PY - 2008/8/18

Y1 - 2008/8/18

N2 - (Chemical Equation Presented) Water, water, everywhere: The title reaction predominantly affords the exo isomer with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). The synthesis can be carried out without organic solvents and provides the products by distillation. Water increases the rate and enantioselectivity of the reaction.

AB - (Chemical Equation Presented) Water, water, everywhere: The title reaction predominantly affords the exo isomer with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). The synthesis can be carried out without organic solvents and provides the products by distillation. Water increases the rate and enantioselectivity of the reaction.

KW - Asymmetric synthesis

KW - Cycloaddition

KW - Enantioselectivity

KW - Organocatalysis

KW - Water chemistry

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JF - Angewandte Chemie - International Edition

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ER -

Asymmetric diels-alder reactions of α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water

Abstract

Keywords

ASJC Scopus subject areas

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