Use of acyl phosphonates as a coupling partner for rhodium-catalyzed [2+2+2] cycloaddition: Unexpected dependence of the reactivity on structures of α,ω-diynes

Synlett

Volumn , Issue 13, 2008, Pages 2017-2022

  Tanaka, Ken ^a   Tanaka, Rie ^a   Nishida, Goushi ^a   Hirano, Masao ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Acylphosphonates; Alkynes; Cycloaddition; H8 BINAP; Rhodium

Indexed keywords

ACYL PHOSPHONIC ACID DERIVATIVE; ALKYNE DERIVATIVE; ALPHA,OMEGA DIYNE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; RHODIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; OLEFINATION;

EID: 49749116849     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077968     Document Type: Article

References (39)

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33. 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) Gakis, N.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1975, 58, 748. For hetero-Diels-Alder reactions involving α,β-unsaturated acyl phosphonates, see:
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37. In general, terminal alkynes are more reactive and coordinative toward rhodium than internal alkynes. Therefore, the reaction of terminal 1,6-diyne 1d with 2b results in the rapid homo-[2+2+2] cycloaddition of 1d via a rhodacyclopentadiene intermediate. On the other hand, the formation of the rhodacyclopentadiene intermediate from terminal 1,7-diyne 1h may be slower than that from terminal 1,6-diynes for steric reasons. Thus, the reaction of 1h with 2b may furnish the oxarhodacyclopentene intermediate. Insertion of another terminal alkyne moiety of 1h followed by reductive elimination of rhodium furnishes the corresponding cross-[2+2+2] cycloaddition product 3hb in good yield.
38. Equilibrium coordination of the ester carbonyl oxygen vs. the alkyne moiety of a malonate-linked 1,6-diyne is proposed in the Ru-catalyzed [2+2+2] cycloaddition of alkynes, see: Yamamoto, Y.; Arakawa, T.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2003, 125, 12143.
39. 3): δ = 14.5. Compound (2)-3ab: pale yellow oil.