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Volumn 51, Issue 52, 2012, Pages 13031-13035

Rhodium-catalyzed regio-, diastereo-, and enantioselective [2+2+2] cycloaddition of 1,6-enynes with acrylamides

Author keywords

Asymmetric catalysis; Cycloaddition; Cyclohexenes; Enynes; Rhodium

Indexed keywords

1 ,6-ENYNES; [2+2+2] CYCLOADDITION; ACRYLAMIDES; ASYMMETRIC CATALYSIS; ASYMMETRIC VARIANTS; BISPHOSPHINE; CARBON-CARBON BOND-FORMING REACTIONS; CYCLOADDITIONS; CYCLOHEXADIENES; CYCLOHEXENES; ELECTRON-DEFICIENT; ENANTIOSELECTIVE; ENYNES; FACILE PREPARATION; INTRAMOLECULAR REACTIONS; MONTGOMERY; REACTIVE SUBSTRATES; RESEARCH GROUPS; RHODIUM-CATALYZED; SINGLE-STEP; STEREOGENIC CENTERS;

EID: 84871962315     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206122     Document Type: Article
Times cited : (45)

References (66)
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    • For selected recent reviews of the transition-metal-catalyzed [2+2+2] cycloadditions, see: a) S. Okamoto, Heterocycles 2012, 85, 1579
    • (2012) Heterocycles , vol.85 , pp. 1579
    • Okamoto, S.1
  • 30
    • 84856230859 scopus 로고    scopus 로고
    • For reviews of the rhodium-catalyzed [2+2+2] cycloadditions, see: a) Y. Shibata, K. Tanaka, Synthesis 2012, 323
    • Synthesis , vol.2012 , pp. 323
    • Shibata, Y.1    Tanaka, K.2
  • 37
    • 34250727598 scopus 로고    scopus 로고
    • for the Rh-catalyzed [2+2+2] cycloaddition of 1,6-diynes with dimethyl fumarate to construct two stereogenic centers, see: d) K. Tanaka, G. Nishida, H. Sagae, M. Hirano, Synlett 2007, 1426.
    • (2007) Synlett , pp. 1426
    • Tanaka, K.1    Nishida, G.2    Sagae, H.3    Hirano, M.4
  • 55
  • 56
    • 84871995889 scopus 로고    scopus 로고
    • The reactions of 1,6-enynes 1a and 1h with crotonamide 2h and methacrylamide 2i were also examined, and the desired [2+2+2] cycloaddition products were not obtained at all instead the corresponding homo-[2+2+2] cycloaddition products of 1a and 1h were generated
    • The reactions of 1,6-enynes 1a and 1h with crotonamide 2h and methacrylamide 2i were also examined, and the desired [2+2+2] cycloaddition products were not obtained at all instead the corresponding homo-[2+2+2] cycloaddition products of 1a and 1h were generated.
  • 57
    • 84871983816 scopus 로고    scopus 로고
    • A Similar Regioselective Formation Of Rhodacyclopentene G Possessing The Alkoxycarbonyl Group At The Sp3-Hybridized Carbon Atom Adjacent To Rhodium Was Proposed In The Cationic Rhodium (I)/(R)-H8-binap-catalyzed dimerization of acrylates with internal alkynes
    • A similar regioselective formation of rhodacyclopentene G, possessing the alkoxycarbonyl group at the sp3-hybridized carbon atom adjacent to rhodium, was proposed in the cationic rhodium(I)/(R)-H8-binap-catalyzed dimerization of acrylates with internal alkynes
  • 59
    • 0343953463 scopus 로고    scopus 로고
    • In general, the cycloaddition reactions of 1,6-enynes via rhodacyclopentene A are highly enantioselective. For representative examples of the asymmetric [2+2+1] cycloadditions (Pauson-Khand reactions), see: a) N. Jeong, B. K. Sung, Y. K. Choi, J. Am. Chem. Soc. 2000, 122, 6771
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6771
    • Jeong, N.1    Sung, B.K.2    Choi, Y.K.3
  • 61
    • 84871994427 scopus 로고    scopus 로고
    • for examples of the asymmetric [2+2+2] cycloadditions, see: references [3] and [9b-d]. Similarly, the reaction of 1j and 2a furnished the corresponding cyclohexene 3ja with a high ee value and the corresponding diene 4ja with a low ee value, although 4ja could not been isolated in a pure form by silica gel chromatography
    • for examples of the asymmetric [2+2+2] cycloadditions, see: references [3] and [9b-d]. Similarly, the reaction of 1j and 2a furnished the corresponding cyclohexene 3ja with a high ee value and the corresponding diene 4ja with a low ee value, although 4ja could not been isolated in a pure form by silica gel chromatography.
  • 66
    • 84871961965 scopus 로고    scopus 로고
    • CCDC 894213 ((-)-7eb) and 894214 ((-)-8aa) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 894213 ((-)-7eb) and 894214 ((-)-8aa) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.