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: purchase@heterocycles.com

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

Short Paper | Regular issue | Vol 98, No. 12, 2019, pp.1725-1735
Published online, 17th December, 2019
DOI: 10.3987/COM-19-14180
Chemoselectivity-Tunable [5 + 2] Cycloadditions of Allenamides and Oxidopyryliums

Min Yang, Liangliang Kang, and Shuzhong He*

*School of Pharmaceutical Sciences, Guizhou University, 440 Chongyi Building,Guizhou University, Huaxi District, China

Abstract

[5 + 2] Cycloadditions between allenamides and oxidopyryliums are described. A series of substituted cycloheptanones were synthesized by this method with moderate to good yields. Interestingly, the chemoselectivity of this reaction could be tuned by changing the electron-withdrawing groups on the allenamide nitrogen atom. When oxazolidinone chiral auxiliaries were introduced in the allenamide substrate, [5 + 2] cycloadducts could be obtained with high diastereoselectivities. This reaction provides a useful synthetic protocol for the construction of highly substituted seven-membered rings.