Diastereoselective syntheses of functionalized five-membered carbocycles and heterocycles by a SmI2-promoted intramolecular coupling of bromoalkynes and α,β-unsaturated esters

Organic Letters

Volumn 12, Issue 13, 2010, Pages 3026-3029

  Takahashi, Kazunori ^a   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BROMINATED HYDROCARBON; ESTER; HETEROCYCLIC COMPOUND; HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; ESTERS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, BROMINATED; HYDROCARBONS, CYCLIC; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77954117148     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101034s     Document Type: Article

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53. When the phenylacetylene derivative was subjected to the same reaction, the (Z)-benzylidene derivative (Z -3b) was obtained as a major compound (58%, Z: E = 88:12). On the other hand, a similar reaction of alkyl-substituted alkynes did not give any coupling products. Thus, it is assumed that the substituents on alkynes contributing to stabilization of radicals generated as intermediates is important for this type of cyclization.