Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters

Journal of the American Chemical Society

Volumn 131, Issue 33, 2009, Pages 11654-11655

  Shapiro, Nathan D ^a   Shi, Yun ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOIDS; CHEMICAL EQUATIONS; CYCLOADDITION REACTION; PROPARGYL; STARTING MATERIALS;

CYCLOADDITION; ESTERIFICATION; GOLD; NITROGEN COMPOUNDS;

ESTERS;

AZOMETHINE IMINE DERIVATIVE; ESTER DERIVATIVE; GOLD; IMINE; PROPARGYLESTER DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION;

AZO COMPOUNDS; CATALYSIS; ESTERS; GOLD; IMINES; THIOSEMICARBAZONES;

EID: 69049113944     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903863b     Document Type: Article

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40. Additional evidence for a stepwise mechanism was obtained in the reaction of azomethine imine 11, which furnished enamine 12 after ring fragmentation and tautomerization. (Chemical Equation Presented)
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42. This substrate combination was chosen to aid in characterization of the products. Nearly identical selectivites were observed in reactions employing either 8a or 8c.
43. The configuration of the minor isomer was confirmed by X-ray crystallography (see Supporting Information).
44. For further synthetic transformations of the diazabicycles, see the Supporting Information.