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An Allene Approach to Tetrahydrofuran‐Fused Bicyclo[2.2.2]oct‐2‐enes
Author(s) -
Song Shihua,
Fu Chunling,
Huang Xin,
Ma Shengming
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701407
Subject(s) - chemistry , allene , bicyclic molecule , tetrahydrofuran , substituent , enantiomer , malononitrile , oxygen , medicinal chemistry , stereochemistry , organic chemistry , catalysis , solvent
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.