Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans

A novel tandem cross-Rauhut–Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative c...

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Bibliographic Details
Published in:Tetrahedron 2011-03, Vol.67 (10), p.1768-1773
Main Authors: Liu, Wen, Zhou, Jing, Zheng, Changwu, Chen, Xingkuan, Xiao, Hua, Yang, Yingquan, Guo, Yinlong, Zhao, Gang
Format: Article
Language:English
Subjects:
3,4-Dihydropyrans
Activated
Activated alkenes
Alkenes
Catalysis
Catalysts
Catalysts: preparations and properties
Chemistry
Cyclization reaction
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Ketones
Organic chemistry
Preparations and properties
Rauhut–Currier reaction
Stereoselectivity
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:A novel tandem cross-Rauhut–Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.01.036