Pd-Catalyzed Allylic Alkylation Cascade with Dihydropyrans: Regioselective Synthesis of Furo[3,2-c]pyrans
Pd-Catalyzed Allylic Alkylation Cascade with Dihydropyrans: Regioselective Synthesis of Furo[3,2-c]pyrans
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DOI：
10.1021/ol400902d
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发表时间：
2013-05-17
期刊：
影响因子：
5.2
通讯作者：
Harvey, Joanne E.
中科院分区：
文献类型：
--
作者：
Bartlett, Mark J.;Turner, Claire A.;Harvey, Joanne E.
钯催化的烯丙基烷基化级联反应是由不同的环状β-二羰基双亲核试剂和3，6-二氢-2H-吡喃双亲电体合成的呋喃[3，2-c]吡喃。二氢吡喃底物中的烯丙基碳酸酯和异构体硅氧基离开基团的组合允许控制该反应中的许多区域化学可能性。环化以立体聚合的方式进行，从顺式或反式取代的原料中得到顺式稠合呋喃。
A regioselective palladium-catalyzed allylic alkylation cascade forms furo[3,2-c]pyrans from various cyclic beta-dicarbonyl bis-nucleophiles and 3,6-dihydro-2H-pyran bis-electrophiles. The combination of allylic carbonate and anomeric siloxy leaving groups in the dihydropyran substrate allows control of the many regiochemical possibilities in this reaction. Annulation proceeds stereoconvergently to give cis-fused furopyrans from either cis- or trans-substituted starting material.