Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 83, No. 11, 2011, pp.2525-2534
Published online, 8th September, 2011
DOI: 10.3987/COM-11-12322
Novel Sulfonamide Catalyzed Asymmetric Hetero-Diels-Alder Reaction of Ethyl Glyoxylate with Danishefsky’s Diene

Takuya Kanemitsu, Yasufumi Asajima, Takashi Shibata, Michiko Miyazaki, Kazuhiro Nagata, and Takashi Itoh*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan


Novel sulfonamide organocatalysts were prepared from chiral Betti base and various sulfonyl chlorides, and applied to the asymmetric hetero-Diels–Alder reaction of ethyl glyoxylate with Danishefsky's diene. The sulfonamides exhibited catalytic activity as hydrogen bond donor. In particular, sulfonamide 3g showed highest catalytic performance for the reaction. Sulfonamide 3g catalyzed asymmetric reaction followed by treatment with TFA obtained corresponding 6-substituted 2,3-dihydropyran-4-ones in moderate yield and enantioselectivity.