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Rhodium‐Catalyzed [5+2] Cycloaddition of 3‐Acyloxy‐1,4‐enyne with Alkene or Allene
Author(s) -
Song Wangze,
Lynch John C.,
Shu Xingzhong,
Tang Weiping
Publication year - 2016
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.201600196
Subject(s) - allene , stereocenter , enyne , cycloaddition , chemistry , alkene , rhodium , bicyclic molecule , intramolecular force , catalysis , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis
We recently developed a completely new type of Rh‐catalyzed [5+2] cycloaddition by using 3‐acyloxy‐1,4‐enyne (ACE) as the 5‐carbon building block. In this update, we show that ACE can undergo intramolecular [5+2] cycloaddition with either an alkene or an allene in the presence of an appropriate rhodium catalyst and ligands to afford bicyclic compounds with multiple stereogenic centers. In most cases, cis ‐fused bicyclo[5.3.0]decadienes are prepared highly diastereoselectively.