Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C, N-cyclic azomethine imines. Issue 36 (4th September 2017)

• Record Type: Journal Article
• Authors: Xu, Jianfeng; Yuan, Shiru; Peng, Jingyi; Miao, Maozhong; Chen, Zhengkai; Ren, Hongjun
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 36(2017)
• Page Start: 7513
• Page End: 7517
• Publication Date: 2017-09-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01783a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient base-mediated [4 + 3] annulation reaction of ortho -quinone methides with C, N -cyclic azomethine imines is disclosed. 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.