Organocatalytic asymmetric nitroaldol reaction: cooperative effects of guanidine and thiourea functional groups.

Organocatalytic asymmetric nitroaldol reaction: cooperative effects of guanidine and thiourea functional groups. Research Abstract Details 

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Organocatalytic asymmetric nitroaldol reaction: cooperative effects of guanidine and thiourea functional groups. Abstract Text:

Yoshihiro Sohtome,Nobuko Takemura,Keisuke Takada,Rika Takagi,Toshitsugu Iguchi,Kazuo Nagasawa,Yoshihiro Sohtome,Nobuko Takemura,Keisuke Takada,Rika Takagi,Toshitsugu Iguchi,Kazuo Nagasawa,

Catalytic enantio- and diastereoselective nitroaldol reactions were explored by using designed guanidine-thiourea bifunctional organocatalysts under mild and operationally simple biphasic conditions. These catalytic asymmetric reactions have a broad substrate generality with respect to the variety of aldehydes and nitroalkanes. Based on this catalytic nitroaldol process, straightforward syntheses of cytoxazone and 4-epi-cytoxazone were achieved. These catalytic nitroaldol reactions require KI as an additive for highly asymmetric induction; it operates by inhibiting the retro mode of the reaction. On the basis of studies of structure and catalytic-activity relationships, a plausible guanidine-thiourea cooperative mechanism and a transition state of the catalytic reactions are proposed. Drastic substituent effects on the catalytic properties of this catalyst may lead to the development of new chiral surfactants.

Organocatalytic asymmetric nitroaldol reaction: cooperative effects of guanidine and thiourea functional groups. Publishing Authors By Initials

Y Sohtome,N Takemura,K Takada,R Takagi,T Iguchi,K Nagasawa,Y Sohtome,N Takemura,K Takada,R Takagi,T Iguchi,K Nagasawa,

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Organocatalytic asymmetric nitroaldol reaction: cooperative effects of guanidine and thiourea functional groups. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Chemistry, an Asian journal

VOLUME: 2

Page Numbers: 1150-60

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ISSN: 1861-471X

DAY: 3

MONTH: Sep

YEAR: 2007

Organocatalytic asymmetric nitroaldol reaction: cooperative effects of guanidine and thiourea functional groups. Information

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LANGUAGE: eng

NlmUniqueID: 101294643

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Grant and Affiliation Information for Organocatalytic asymmetric nitroaldol reaction: cooperative effects of guanidine and thiourea functional groups.

AFFILIATION: Graduate School of Pharmaceutical Science, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Country: Germany

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MEDLINETA: Chem Asian J

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