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Synfacts 2014; 10(9): 0944
DOI: 10.1055/s-0034-1378981
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Hetero-Diels–Alder Reaction of Danishefsky’s Diene with Keto Esters

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
Hu Y, Xu K, Zhang S, Guo F, Zha Z, Wang Z * University of Science and Technology of China, Hefei, P. R. of China
Copper-Catalyzed Enantioselective Hetero-Diels–Alder Reaction of Danishefsky’s Diene with β,γ-Unsaturated α-Ketoesters.

Org. Lett. 2014;
16: 3564-3567
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Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

hetero-Diels–Alder reaction - Danishefsky’s diene - copper

Significance

The authors present the copper-catalyzed asymmetric hetero-Diels–Alder reaction of Danishefsky’s diene with β,γ-unsaturated α-keto esters. A series of chiral dihydropyranones were prepared in good yields (up to 99%) with ­excellent enantioselectivities (up to 97% ee).


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Comment

The authors demonstrate that the reaction pathway is substrate-dependent. In the case of alkenyl α-keto esters, the reaction proceeds via a concerted pathway. On the other hand, a stepwise pathway is involved in the reaction of alkynyl α-keto esters.


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