Rhodium-Catalyzed [5+2] Cycloaddition of 3-Acyloxy-1,4-enyne with Alkene or Allene

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 rhod...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 358; no. 12; pp. 2007 - 2011
Main Authors Song, Wangze, Lynch, John C., Shu, Xing-zhong, Tang, Weiping
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 16.06.2016
WILEY‐VCH Verlag
Wiley
Subjects
Allene
allenes
Catalysis
Catalysts
Chemistry
Chemistry, Applied
Chemistry, Organic
Cycloaddition
enynes
Ligands
Olefins
Physical Sciences
Rhodium
Science & Technology
Synthesis
MECHANISTIC ASPECTS
VINYL AZIRIDINES
catalysis
VINYLCYCLOPROPANES
enynes
ALKYNES
allenes
cycloaddition
NATURAL-PRODUCT SYNTHESIS
7-MEMBERED RINGS
DIELS-ALDER REACTION
4C+3C
METAL
CHIRALITY
rhodium
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Summary: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.
Bibliography:UW School of Pharmacy
Wisconsin Alumni Research Foundation (WARF)
istex:FED905520CAF8EC0CCB9220E85026920CA1CA9B3
ark:/67375/WNG-GSPJB7M5-L
University of Wisconsin-Madison
NSF - No. CHE-1464754
ArticleID:ADSC201600196
National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600196