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Synfacts 2014; 10(1): 0092
DOI: 10.1055/s-0033-1340403
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Arylation of Enecarbamates with Quinone Imine Ketals

Contributor(s):
Benjamin List
,
Ji Hye Kim
Hashimoto T, Nakatsu H, Takiguchi Y, Maruoka K * Kyoto University, Japan
Axially Chiral Dicarboxylic Acid Catalyzed Activation of Quinone Imine Ketals: Enantioselective Arylation of Enecarbamates.

J. Am. Chem. Soc. 2013;
135: 16010-16013
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

enecarbamates - dicarboxylic acids - quinone imine ketals

Significance

The asymmetric enantioselective arylation of enecarbamates catalyzed by a chiral Brønsted acid is reported. An axially chiral dicarboxylic acid (1) catalyzes the reaction of quinone imine ketals 2 with enecarbamates 3 to give α-amino-β-aryl ethers 4 in good yields and enantio­selectivities. The products could be transformed into various useful chiral building blocks.


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Comment

It is notable that opposite enantiomers of the products are obtained by changing from Z- to E-enecarbamates. The authors propose that the isomeric enecarbamates approach the quinone imine ketals 2 from the same prochiral face, and that diastereomeric intermediates are generated that lead to the opposite enantiomers after aromatization.


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