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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Veröffentlicht in:	Tetrahedron 2011-03, Vol.67 (10), p.1768-1773
Hauptverfasser:	Liu, Wen, Zhou, Jing, Zheng, Changwu, Chen, Xingkuan, Xiao, Hua, Yang, Yingquan, Guo, Yinlong, Zhao, Gang
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Zusammenfassung:	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