An Allene Approach to Tetrahydrofuran-Fused Bicyclo[2.2.2]oct-2-enes

作者：Song, Shihua; Fu, Chunling; Huang, Xin^*; Ma, Shengming^*

来源：Advanced Synthesis & Catalysis, 2018, 360(5): 1019-1025.

DOI：10.1002/adsc.201701407

• palladium
• polycycle
• allene
• 2,7-alkadiynylic carbonates

An efficient access to tetrahydrofuran-fused bicyclo[2.2.2]oct-2-enes via palladium-catalyzed cyclization of oxygen-tethered 2,7-alkadiynylic carbonates with 2-(buta-2,3-dienyl)malononitrile has been developed. Perfect chiral induction was observed when a substituent was introduced to the propargylic position affording the optically active polycyclic products of both enantiomers. Control experiments showed that the oxygen tether of 2,7-alkadiynylic carbonates and the two cyano groups in allene are indispensible for this transformation.

• 出版日期2018-3-1
• 单位浙江大学