Pd-Catalyzed Allylic Alkylation Cascade with Dihydropyrans: Regioselective Synthesis of Furo[3,2-c]pyrans

被引：38
|
作者：
Bartlett, Mark J. [1 ]
Turner, Claire A. [1 ]
Harvey, Joanne E. [1 ]
机构：
[1] Victoria Univ Wellington, Sch Chem & Phys Sci, Wellington 6140, New Zealand
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 10期
关键词：
ASYMMETRIC-SYNTHESIS; ATOM ECONOMY; C-O; PALLADIUM; DERIVATIVES; CONSTRUCTION; HUPERZINE; STEREOCHEMISTRY; SUBSTITUTIONS; NUCLEOPHILES;
D O I：
10.1021/ol400902d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：2430 / 2433
页数：4
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