Asymmetric aldol reaction of chloral catalyzed by diarylprolinol

Yujiro Hayashi; Shoya Watanabe; Yusuke Yasui; Shigenobu Umemiya

doi:10.1002/cctc.201500282

Asymmetric aldol reaction of chloral catalyzed by diarylprolinol

Yujiro Hayashi, Shoya Watanabe, Yusuke Yasui, Shigenobu Umemiya

SCI - Chemistry

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

10 Citations (Scopus)

Abstract

The asymmetric cross-aldol reaction of chloral hydrate with aldehyde pronucleophiles catalyzed by a trifluoromethyl-substituted diarylprolinol was accomplished to afford γ-trichloro-β-hydroxy aldehydes in good yields with excellent enantioselectivities. The resulting aldehyde products were converted into chiral α-azido, α-(4-methyl)phenoxy, and α-fluoro esters without a loss in the diastereo- or enantioselectivities.

Original language	English
Pages (from-to)	1646-1649
Number of pages	4
Journal	ChemCatChem
Volume	7
Issue number	11
DOIs	https://doi.org/10.1002/cctc.201500282
Publication status	Published - 2015 Jun 1

Keywords

aldehydes
aldol reaction
asymmetric synthesis
chloral
organocatalysis

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1002/cctc.201500282

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title = "Asymmetric aldol reaction of chloral catalyzed by diarylprolinol",

abstract = "The asymmetric cross-aldol reaction of chloral hydrate with aldehyde pronucleophiles catalyzed by a trifluoromethyl-substituted diarylprolinol was accomplished to afford γ-trichloro-β-hydroxy aldehydes in good yields with excellent enantioselectivities. The resulting aldehyde products were converted into chiral α-azido, α-(4-methyl)phenoxy, and α-fluoro esters without a loss in the diastereo- or enantioselectivities.",

keywords = "aldehydes, aldol reaction, asymmetric synthesis, chloral, organocatalysis",

author = "Yujiro Hayashi and Shoya Watanabe and Yusuke Yasui and Shigenobu Umemiya",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

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doi = "10.1002/cctc.201500282",

language = "English",

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journal = "ChemCatChem",

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TY - JOUR

T1 - Asymmetric aldol reaction of chloral catalyzed by diarylprolinol

AU - Hayashi, Yujiro

AU - Watanabe, Shoya

AU - Yasui, Yusuke

AU - Umemiya, Shigenobu

PY - 2015/6/1

Y1 - 2015/6/1

N2 - The asymmetric cross-aldol reaction of chloral hydrate with aldehyde pronucleophiles catalyzed by a trifluoromethyl-substituted diarylprolinol was accomplished to afford γ-trichloro-β-hydroxy aldehydes in good yields with excellent enantioselectivities. The resulting aldehyde products were converted into chiral α-azido, α-(4-methyl)phenoxy, and α-fluoro esters without a loss in the diastereo- or enantioselectivities.

AB - The asymmetric cross-aldol reaction of chloral hydrate with aldehyde pronucleophiles catalyzed by a trifluoromethyl-substituted diarylprolinol was accomplished to afford γ-trichloro-β-hydroxy aldehydes in good yields with excellent enantioselectivities. The resulting aldehyde products were converted into chiral α-azido, α-(4-methyl)phenoxy, and α-fluoro esters without a loss in the diastereo- or enantioselectivities.

KW - aldehydes

KW - aldol reaction

KW - asymmetric synthesis

KW - chloral

KW - organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=85027928512&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027928512&partnerID=8YFLogxK

U2 - 10.1002/cctc.201500282

DO - 10.1002/cctc.201500282

M3 - Article

AN - SCOPUS:85027928512

SN - 1867-3880

VL - 7

SP - 1646

EP - 1649

JO - ChemCatChem

JF - ChemCatChem

IS - 11

ER -

Asymmetric aldol reaction of chloral catalyzed by diarylprolinol

Abstract

Keywords

ASJC Scopus subject areas

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