Jump to main content
Jump to site search

Issue 36, 2017
Previous Article Next Article

Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines

Author affiliations

Abstract

An efficient [4 + 3] annulation of 2-(1-tosylalkyl)phenols with C,N-cyclic azomethine imines via in situ generation of ortho-quinone methides (o-QMs) under mild basic reaction conditions is disclosed, furnishing biologically interesting seven-membered heterocyclic compounds with moderate to good yields and excellent diastereoselectivities. A gram-scale reaction is performed to demonstrate the potential in industrial application and two transition states are proposed to rationalize the outstanding diastereoselectivity.

Graphical abstract: Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Jul 2017, accepted on 28 Aug 2017 and first published on 29 Aug 2017


Article type: Communication
DOI: 10.1039/C7OB01783A
Citation: Org. Biomol. Chem., 2017,15, 7513-7517
  •   Request permissions

    Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines

    J. Xu, S. Yuan, J. Peng, M. Miao, Z. Chen and H. Ren, Org. Biomol. Chem., 2017, 15, 7513
    DOI: 10.1039/C7OB01783A

Search articles by author

Spotlight

Advertisements