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Synthesis 2017; 49(09): 2035-2044
DOI: 10.1055/s-0036-1588935
DOI: 10.1055/s-0036-1588935
paper
Organocatalytic Generation of o-Quinone Methides from Commonly Used o-Hydroxystyrenes at High Temperature for Enantioselective Cyclization
Further Information
Publication History
Received: 29 November 2016
Accepted after revision: 15 December 2016
Publication Date:
24 January 2017 (online)
Abstract
o-Quinone methides generated at high temperature under organocatalysis from commonly used o-hydroxystyrenes undergo enantioselective cyclization with dimedone-derived enaminones, to form biologically important tetrahydroxanthenes in high yields and good enantioselectivities (up to 88% yield, 95:5 er). The reaction proceeds in chlorobenzene in the presence of a chiral phosphoric acid (CPA) at 110 °C. The reaction scope with regard to various ring-substituted o-hydroxystyrenes and various N-aryl-substituted enaminones was investigated. In addition, this reaction also provided an efficient method for constructing chiral tetrahydroxanthene scaffolds.
Key words
organocatalysis - enantioselectivity - asymmetric synthesis - o-quinone methide - o-hydroxystyreneSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588935.
- Supporting Information
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References
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For substitutions, see:
For cycloadditions, see:
For a review, see:
For some representative examples, see:
For some recent reviews containing o-QM-involved catalytic enantioselective reactions, see:
For some recent examples of o-QM-involved catalytic enantioselective cyclizations, see:
For some reviews, see: