Diarylprolinol in an asymmetric, direct cross-aldol reaction with alkynyl aldehydes

Yujiro Hayashi; Masahiro Kojima; Yusuke Yasui; Yuta Kanda; Takasuke Mukaiyama; Hiroki Shomura; Daichi Nakamura; Ritmaleni; Itaru Sato

doi:10.1002/cctc.201300390

Diarylprolinol in an asymmetric, direct cross-aldol reaction with alkynyl aldehydes

Yujiro Hayashi, Masahiro Kojima, Yusuke Yasui, Yuta Kanda, Takasuke Mukaiyama, Hiroki Shomura, Daichi Nakamura, Ritmaleni, Itaru Sato

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

16 Citations (Scopus)

Abstract

The direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical route for the highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity were obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks. Reacts like a Pro: The asymmetric, direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical and highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity are obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks.

Original language	English
Pages (from-to)	2887-2892
Number of pages	6
Journal	ChemCatChem
Volume	5
Issue number	10
DOIs	https://doi.org/10.1002/cctc.201300390
Publication status	Published - 2013 Oct

Keywords

Aldehydes
Aldol reaction
Alkynes
Asymmetric synthesis
Organocatalysis

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Diarylprolinol in an asymmetric, direct cross-aldol reaction with alkynyl aldehydes",

abstract = "The direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical route for the highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity were obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks. Reacts like a Pro: The asymmetric, direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical and highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity are obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks.",

keywords = "Aldehydes, Aldol reaction, Alkynes, Asymmetric synthesis, Organocatalysis",

author = "Yujiro Hayashi and Masahiro Kojima and Yusuke Yasui and Yuta Kanda and Takasuke Mukaiyama and Hiroki Shomura and Daichi Nakamura and Ritmaleni and Itaru Sato",

year = "2013",

month = oct,

doi = "10.1002/cctc.201300390",

language = "English",

volume = "5",

pages = "2887--2892",

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T1 - Diarylprolinol in an asymmetric, direct cross-aldol reaction with alkynyl aldehydes

AU - Hayashi, Yujiro

AU - Kojima, Masahiro

AU - Yasui, Yusuke

AU - Kanda, Yuta

AU - Mukaiyama, Takasuke

AU - Shomura, Hiroki

AU - Nakamura, Daichi

AU - Ritmaleni,

AU - Sato, Itaru

PY - 2013/10

Y1 - 2013/10

N2 - The direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical route for the highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity were obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks. Reacts like a Pro: The asymmetric, direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical and highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity are obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks.

AB - The direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical route for the highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity were obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks. Reacts like a Pro: The asymmetric, direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical and highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity are obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks.

KW - Aldehydes

KW - Aldol reaction

KW - Alkynes

KW - Asymmetric synthesis

KW - Organocatalysis

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U2 - 10.1002/cctc.201300390

DO - 10.1002/cctc.201300390

M3 - Article

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VL - 5

SP - 2887

EP - 2892

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

IS - 10

ER -

Diarylprolinol in an asymmetric, direct cross-aldol reaction with alkynyl aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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