Metal iodide mediated ring expansion of cyclopropanecarboxylic thioesters with imines

Tetrahedron Letters

Volumn 47, Issue 28, 2006, Pages 4911-4915

  Huang, Wenwei ^a   Chin, Janice ^a   Karpinski, Luke ^a   Gustafson, Gary ^a   Baldino, Carmen M ^a   Yu, Libing ^a  

^a ARQULE INC   (United States)

Author keywords

Pyrrolidine; Retro aza Michael addition; Thioester; Three component reaction

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; IMINE; IODIDE; LACTAM DERIVATIVE; METAL; PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; METHODOLOGY; MICHAEL ADDITION;

EID: 33744789414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.019     Document Type: Article

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16. 2a When a mixture of 2a and 3a was used, the reaction gave phenylketones 5 and 6 as a pair of cis-trans isomers (Eq. 1). The proton NMR spectra of the phenylketones were compared with those of the authentic samples. Under the same condition, thioester 2a gave phenylketone 5, the trans isomer (Eq. 2). Based on these observations, 2a was tentatively assigned as trans configuration.(1)(2)
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