Synthesis of multisubstituted 2-(dihydrofuran-2(3H)-ylidene)acetates via intramolecular carboalkoxylation by platinum-olefin catalyst system

被引:36
作者
Nakamura, Itaru [1 ]
Chan, Ching Siew [1 ]
Araki, Toshiharu [1 ]
Terada, Masahiro [1 ]
Yamamoto, Yoshinori [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/ol702795u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclization of 6-(1-alkoxyethyl)hex-2-ynoates in the presence of a platinum-olefin catalyst system gave the corresponding multisubstituted 2-(dihydrofuran-2(3H)-ylidene)acetates in good to high yields. The Z/E selectivity is controlled by the electronic property of the ester group; the 2,2,2-trichloroethyl ester led to the Z isomer, while the phenyl ester gave the E isomer.
引用
收藏
页码:309 / 312
页数:4
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