Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine iminesElectronic supplementary information (ESI) available: Experimental procedures and characterization data. CCDC 1553421. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ob01783a

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 go...

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Main Authors: Xu, Jianfeng, Yuan, Shiru, Peng, Jingyi, Miao, Maozhong, Chen, Zhengkai, Ren, Hongjun
Format: Article
Language:English
Online Access:Get full text
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Summary: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. An efficient base-mediated [4 + 3] annulation reaction of ortho -quinone methides with C , N -cyclic azomethine imines is disclosed.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01783a