Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Reviews and Accounts
Asymmetric Syntheses Utilizing Mild Activations by Organocatalysts
Keisuke Asano
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2016 Volume 74 Issue 12 Pages 1194-1205

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Abstract

Organocatalysts utilize various molecular interactions for catalysis. However, molecular interactions for organocatalysis are in general not as strong as those for metal-catalysis. Thus, because of this character, multiple activations are often necessary to catalyze a reaction, however, in other words, it enables the use of multipoint interactions in the transition state of a catalytic reaction, thereby leading to high stereoselectivity, even if it is a very rapid reaction. On the basis of this concept, we developed asymmetric reactions affording various heterocycles via organocatalytic hetero-Michael additions and the applied synthetic transformations. In order to accomplish high enantioselectivity, we designed reactions utilizing different activation manners by organocatalysts depending on the substrate type; it is a key to utilize simultaneous multipoint interactions between a catalyst and a substrate.

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© 2016 The Society of Synthetic Organic Chemistry, Japan
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