Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions

Yuko Okuyama; Hiroto Nakano; Yuki Watanabe; Mika Makabe; Mitsuhiro Takeshita; Koji Uwai; Chizuko Kabuto; Eunsang Kwon

doi:10.1016/j.tetlet.2008.10.122

Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions

Yuko Okuyama, Hiroto Nakano, Yuki Watanabe, Mika Makabe, Mitsuhiro Takeshita, Koji Uwai, Chizuko Kabuto, Eunsang Kwon

SCI - Research and Analytical Center for Giant Molecules

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

46 Citations (Scopus)

Abstract

4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with high enantioselectivity are supported by a DFT theoretical study of their transition state.

Original language	English
Pages (from-to)	193-197
Number of pages	5
Journal	Tetrahedron Letters
Volume	50
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2008.10.122
Publication status	Published - 2009 Jan 14

Keywords

4-Hydroxy-prolinamide alcohol
Aldol reaction
DFT calculations
Michael reaction
Organocatalyst

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10.1016/j.tetlet.2008.10.122

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title = "Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions",

abstract = "4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with high enantioselectivity are supported by a DFT theoretical study of their transition state.",

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author = "Yuko Okuyama and Hiroto Nakano and Yuki Watanabe and Mika Makabe and Mitsuhiro Takeshita and Koji Uwai and Chizuko Kabuto and Eunsang Kwon",

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T1 - Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions

AU - Okuyama, Yuko

AU - Nakano, Hiroto

AU - Watanabe, Yuki

AU - Makabe, Mika

AU - Takeshita, Mitsuhiro

AU - Uwai, Koji

AU - Kabuto, Chizuko

AU - Kwon, Eunsang

PY - 2009/1/14

Y1 - 2009/1/14

N2 - 4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with high enantioselectivity are supported by a DFT theoretical study of their transition state.

AB - 4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with high enantioselectivity are supported by a DFT theoretical study of their transition state.

KW - 4-Hydroxy-prolinamide alcohol

KW - Aldol reaction

KW - DFT calculations

KW - Michael reaction

KW - Organocatalyst

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DO - 10.1016/j.tetlet.2008.10.122

M3 - Article

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SN - 0040-4039

VL - 50

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EP - 197

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions

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Keywords

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