金（I）催化的联烯基环氧化合物的串联环化反应。
Gold(I)-catalyzed cascade cyclization of allenyl epoxides.
作者信息
Tarselli Michael A, Zuccarello J Lucas, Lee Stephen J, Gagné Michel R
机构信息
Caudill Laboratories, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
出版信息
Org Lett. 2009 Aug 6;11(15):3490-2. doi: 10.1021/ol901391s.
Abstract
Cationic gold(I) phosphite catalysts activate allenes for epoxide cascade reactions. The system is tolerant of numerous functional groups (sulfones, esters, ethers, sulfonamides) and proceeds at room temperature in dichloromethane. The cyclization pathway is sensitive to the substitution pattern of the epoxide and the backbone structure of the A-ring. It is capable of producing medium-ring ethers, fused 6-5 bicyclic, and linked pyran-furan structures. The resulting cycloisomers are reminiscent of structures found in numerous polyether natural products.
摘要
阳离子亚磷酸金（I）催化剂可活化丙二烯以进行环氧化物级联反应。该体系能耐受多种官能团（砜、酯、醚、磺酰胺），并在室温下于二氯甲烷中进行反应。环化途径对环氧化物的取代模式和A环的主链结构敏感。它能够生成中环醚、稠合的6-5双环以及连接的吡喃-呋喃结构。所得的环异构体让人联想到众多聚醚天然产物中发现的结构。
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