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Synthesis 2019; 51(10): 2136-2148
DOI: 10.1055/s-0037-1610691
DOI: 10.1055/s-0037-1610691
paper
Base-Mediated Tandem 1,6-Addition/Cyclization/Isomerization Reactions between para-Quinone Methides and Benzyl Chlorides: Approaches to Diverse Frameworks at Each Cascade Stage
We are grateful to the NSFC (#21302173) and the Education Department of Henan Province (#19A150049) for financial support.Further Information
Publication History
Received: 13 November 2018
Accepted after revision: 08 January 2019
Publication Date:
19 February 2019 (online)
Abstract
Base-mediated stereospecific tandem reactions using para-quinone methides and carbene-like benzyl chlorides are developed. DBU-mediated 1,6-addition/cyclization/isomerization reactions produce triarylsubstituted alkenes in 43–89% yields and Z/E ratios of 5:1 to 35:1 in favor of the Z-isomers. Single-step 1,6-conjugate additions are realized with the mediation of cesium carbonate, and different triaryl chloroethanes are obtained in yields of 41–54% and excellent diastereoselectivities of more than 20:1. In addition, tandem 1,6-addition/cyclization reactions are achieved using tuned 2,4-disubstituted benzyl chlorides to afford diaryl spirocyclopropyl para-dienones in yields of 35–83% and diastereoselectivities of more than 20:1 in favor of the anti-isomers. The transformations from triaryl chloroethanes and spirocyclopropyl para-dienones into triarylsubstituted alkenes are also demonstrated to support the proposed tandem mechanisms.
Key words
benzyl chlorides - para-quinone methides - tandem reactions - triarylsubstituted alkenes - spirocyclopropyl para-dienonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610691.
- Supporting Information
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