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Synfacts 2014; 10(5): 0510
DOI: 10.1055/s-0033-1341151
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Hydrocyanation Using Ru(phgly)2(binap)–MeOLi System

Contributor(s):
Hisashi Yamamoto
,
Yasushi Shimoda
Sakaguchi Y, Kurono N, Yamauchi K, Ohkuma T * Hokkaido University, Sapporo, Japan
Asymmetric Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles with the Ru(phgly)2(binap)-CH3OLi Catalyst System.

Org. Lett. 2014;
16: 808-811
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Publication History

Publication Date:
17 April 2014 (online)

 
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Key words

ruthenium - hydrocyanation - acylpyrroles

Significance

Ohkuma and co-workers have developed a highly enantioselective conjugate hydrocyanation of α,β-unsaturated N-acyl pyrroles catalyzed by the combination of ruthenium complex 1 and lithium methoxide. The amazingly high catalytic activity (substrate/catalyst = 200–2000) is noteworthy.


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Comment

In this system, the authors propose the following reaction mechanism: The lithium cation acts as a Lewis acid to interact with the carbonyl moiety, and the cyanide anion is located near the amino group due to hydrogen bonding, as reported previously (Org. Lett. 2011, 13, 1254). Therefore, a highly enantioselective addition is achieved with a broad range of substrates.


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