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Volumn , Issue 17, 2009, Pages 2737-2747

Cationic rhodium(I)/H8-binap complex catalyzed [2+2+2] cycloadditions of 1,6- And 1,7-diynes with carbonyl compounds

Author keywords

Carbonyl compounds; Cycloaddition; Diynes; Enones; Rhodium

Indexed keywords


EID: 66449091225     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900185     Document Type: Article
Times cited : (33)

References (91)
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    • To the best of our knowledge, only two examples of a cycloaddition reaction using acyl phosphonates as a coupling partner have been reported. For a photochemical cycloaddition with aziridines, see: a) N. Gakis, H. Heimgartner, H. Schmid, Helv. Chim. Acta 1975, 58, 748 - 760.
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    • On the contrary, the double bond of acrolein exclusively reacted with terminal 1,6-diynes in ruthenium-catalyzed [2+2+2] cycloadditions; see: b J. A. Varela, S. G. Rubín, C. González-Rodríguez, L. Castedo, C. Saá, J. Am. Chem. Soc. 2006, 725, 9262 - 9263.
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    • The cyano group exclusively reacted with la in the case of acetyl and benzoyl cyanides; see: ref.[11c
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    • 5-Alkynals spontaneously cyclized to generate intramolecular hydroacylation products (cylopentanones) in the presence of the cationic rhodium(I)/biaryl bisphosphane catalyst at room, temperature; see: K. Takeishi, K. Sugishima, K. Sasaki, K. Tanaka, Chem. Eur. J. 2004, 70, 5681 - 5688.
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    • Equilibrium coordination of the ester carbonyl oxygen atom versus the alkyne moiety of a malonate-linked 1,6-diyne is proposed in the ruthenium-catalyzed [2+2+2] cycloaddition of alkynes; see: Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2003, 125, 12143, 12160
    • Equilibrium coordination of the ester carbonyl oxygen atom versus the alkyne moiety of a malonate-linked 1,6-diyne is proposed in the ruthenium-catalyzed [2+2+2] cycloaddition of alkynes; see: Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2003, 125, 12143 - 12160.
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    • A similar regioselectivity to this was observed in the ruthenium-catalyzed [2+2+2] cycloadditions of 1,6-diynes, possessing a methyl group at the alkyne terminus, with diethyl ketomalonate; see: ref.[3
    • [3]
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.