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Synfacts 2015; 11(6): 0617-0619
DOI: 10.1055/s-0034-1380853
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective 1,4-Addition of Amides with α,β-Unsaturated Carbonyls

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
Suzuki H, Sato I, Yamashita Y, Kobayashi S * The University of Tokyo, Japan
Catalytic Asymmetric Direct-Type 1,4-Addition Reactions of Simple Amides.

J. Am. Chem. Soc. 2015;
137: 4336-4339
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Further Information

Publication History

Publication Date:
18 May 2015 (online)

 
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Key words

1,4-addition - chiral crown ethers - potassium

Significance

Kobayashi and co-workers present asymmetric direct 1,4-addition reactions of simple amides with α,β-unsaturated carbonyl compounds catalyzed by a combination of a potassium base and a chiral crown ether. A series of 1,5-dicarbonyl compounds were prepared with excellent stereoselectivities (anti/syn > 99:1, up to 98% ee).


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Comment

A macrocyclic chiral crown ether was found to be effective for the chiral modification of the potassium cation, and the desired reaction proceeded in excellent yields with outstanding dia­stereo- and enantioselectivities. The products can be converted into useful derivatives, including the formal syntheses of natural products.


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