Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines

Hitoshi Ube; Masahiro Terada

doi:10.1016/j.bmcl.2009.03.097

Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines

Hitoshi Ube, Masahiro Terada

SCI - Chemistry

Tohoku University

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

61 Citations (Scopus)

Abstract

The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.

Original language	English
Pages (from-to)	3895-3898
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	14
DOIs	https://doi.org/10.1016/j.bmcl.2009.03.097
Publication status	Published - 2009 Jul 15

Keywords

Asymmetric catalysis
Guanidine
Henry reaction
Nitroaldol reaction
Organocatalysis

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10.1016/j.bmcl.2009.03.097

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title = "Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines",

abstract = "The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.",

keywords = "Asymmetric catalysis, Guanidine, Henry reaction, Nitroaldol reaction, Organocatalysis",

author = "Hitoshi Ube and Masahiro Terada",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas {\textquoteleft}Advanced Molecular Transformation of Carbon Resources{\textquoteright} (Grant No. 19020006) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We also acknowledge the JSPS Research Fellowship for Young Scientists (H.U.) from the Japan Society for Promotion of Sciences.",

year = "2009",

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doi = "10.1016/j.bmcl.2009.03.097",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines

AU - Ube, Hitoshi

AU - Terada, Masahiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas ‘Advanced Molecular Transformation of Carbon Resources’ (Grant No. 19020006) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We also acknowledge the JSPS Research Fellowship for Young Scientists (H.U.) from the Japan Society for Promotion of Sciences.

PY - 2009/7/15

Y1 - 2009/7/15

N2 - The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.

AB - The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.

KW - Asymmetric catalysis

KW - Guanidine

KW - Henry reaction

KW - Nitroaldol reaction

KW - Organocatalysis

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SN - 0960-894X

VL - 19

SP - 3895

EP - 3898

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 14

ER -

Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines

Abstract

Keywords

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