Gold-Catalyzed Diastereoselective Formal Intermolecular [4+2+1] Cycloaddition of 1,3-Dien-8-yne with Diazo Ester

The first example of gold-catalyzed formal intermolecular [4 + 2 + 1] cycloaddition was developed using 1,3-dien-8-yne as C4 and C2 units and diazo ester as the C1 unit, which provides expedient access to a series of structurally complicated [5.3.0] bicyclic adducts in moderate yields with moderate...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 12; pp. 7694 - 7703
Main Authors Wang, Yu-Jiang, Li, Xiao-Xiao, Chen, Zili
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 19.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,6-ENYNES
ACTIVATION
PLATINUM
CYCLOISOMERIZATION
REARRANGEMENTS
CARBONYL YLIDES
CYCLIZATION
ACCESS
ENYNES
DIAZOESTERS
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Summary:The first example of gold-catalyzed formal intermolecular [4 + 2 + 1] cycloaddition was developed using 1,3-dien-8-yne as C4 and C2 units and diazo ester as the C1 unit, which provides expedient access to a series of structurally complicated [5.3.0] bicyclic adducts in moderate yields with moderate to high diastereoselectivities. The key route involved a cascade process of dienyne cycloisomerization, cyclopropyl gold carbene's trapping, and subsequent divinyl cyclopropane (DVCP) Cope rearrangement.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00146