Rhodium-catalyzed one-pot intermolecular [2 + 2 + 2] trimerization/ asymmetric intramolecular [4 + 2] cycloaddition of two aryl ethynyl ethers and 5-alkynals

Organic Letters

Volumn 14, Issue 23, 2012, Pages 5856-5859

  Miyauchi, Yuta ^a   Noguchi, Keiichi ^a   Tanaka, Ken ^a,b  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84870906820     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3027158     Document Type: Article

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70. In the reactions of Table 1, the homo-[2 + 2 + 2] cycloaddition of 1a leading to benzene 7 and the homodimerization of 2a leading to ester 8 were observed as side reactions. For the formation of 8, see: Tanaka, R.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2010, 132, 1238
71. A possible explanation for the formation of two diastereomers 4ag and 4ag ′ is as follows. At rt, the reaction of 1a and 2g affords E -dienyne 3ag as a predominant stereoisomer. At 80 C, equilibration between E -dienyne 3ag and Z -dienyne 3ag ′ occurs in the presence of the cationic Rh(I) catalyst. (For the cationic Rh(I) complex-catalyzed E / Z isomerization of enones, see: Tanaka, K.; Shoji, T.; Hirano, M. Eur. J. Org. Chem. 2007, 2687.) Although E -dienyne 3ag may be thermodynamically more stable, the cyclization of 3ag may be slow as a result of the steric interaction between the methyl and aryloxyvinyl groups in intermediate F. In contrast, the cyclization of thermodynamically less stable Z -dienyne 3ag ′ may be fast as a result of the formation of less sterically demanding intermediate F ′. The formation of 4ag and 4ag ′ through different rhodacycles F and F ′, respectively, is consistent with their different ee values