Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: Gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center

Journal of the American Chemical Society

Volumn 129, Issue 20, 2007, Pages 6398-6399

  Huang, Xiaogen ^a   Zhang, Liming ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLENE DERIVATIVE; ALPHA METHYLCINNAMALDEHYDE; CARBENE; CARBON; CYCLOPENTANONE DERIVATIVE; CYCLOPENTANONE ENOL ETHER; ETHER; GOLD; METHANOL DERIVATIVE; OXOCARBENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; DIASTEREOISOMER; DIPOLE; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 34249056927     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0717717     Document Type: Article

References (22)

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19. Extensive NMR studies including NOESY-1D experiments were used to establish its structure.
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21. 2O followed by phase separation.
22. The starting enal had a Z/E ratio of 2.3/1. The increase of Z/E ratio in 7 is likely due to the slightly different reactivities of the Z- and E-enal toward α-lithiated allenyl MOM ether.