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Volumn 133, Issue 18, 2011, Pages 6918-6921

Rhodium-catalyzed enantioselective cyclizations of γ-alkynylaldehydes with acyl phosphonates: ligand- and substituent-controlled C-P or C-H bond cleavage

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND CLEAVAGE; CYCLIZATIONS; ENANTIOSELECTIVE; PHOSPHONATES; RH COMPLEXES; RHODIUM-CATALYZED; SEGPHOS;

EID: 79955704294     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201337x     Document Type: Article
Times cited : (45)

References (49)
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    • Transition-metal-catalyzed syntheses of cyclic allylic alcohols with tetrasubstituted alkene component via alkylative or arylative cyclizations of γ-alkynylaldehydes have been reported. Ni: (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9065
    • Oblinger, E.1    Montgomery, J.2
  • 41
    • 53549104121 scopus 로고    scopus 로고
    • We reported that the cationic Rh(I)/H8-BINAP complex can catalyze enantio- and diastereoselective [2+2+2] cycloaddition of 1,6- enynes with ketoesters: Tanaka, K.; Otake, Y.; Sagae, H.; Noguchi, K.; Hirano, M. Angew. Chem., Int. Ed. 2008, 47, 1312.
    • (2008) Angew. Chem., Int. Ed. , Issue.47 , pp. 1312
    • Tanaka, K.1    Otake, Y.2    Sagae, H.3    Noguchi, K.4    Hirano, M.5
  • 43
    • 49749116849 scopus 로고    scopus 로고
    • Cationic Rh(I) complex-catalyzed [2+2+2] and [4+2] cycloadditions involving acyl phosphonates: (a) Tanaka, K.; Tanaka, R.; Nishida, G.; Hirano, M. Synlett 2008, 2017.
    • (2008) Synlett , pp. 2017
    • Tanaka, K.1    Tanaka, R.2    Nishida, G.3    Hirano, M.4
  • 45
    • 77951989490 scopus 로고    scopus 로고
    • Alternatively, the formation of intermediate G via the coupling of Rh with 1 and 2 to generate dioxarhodacycle followed by alkyne insertion cannot be excluded. Ni-catalyzed Tishchenko reactions presumably through dioxanickelacycles: (a) Ogoshi, S.; Hoshimoto, Y.; Ohashi, M. Chem. Commun. 2010, 46, 3354.
    • (2010) Chem. Commun. , vol.46 , pp. 3354
    • Ogoshi, S.1    Hoshimoto, Y.2    Ohashi, M.3
  • 47
  • 48
    • 9244234942 scopus 로고    scopus 로고
    • Cationic Rh(I)/BINAP complex-catalyzed intramolecular hydroacylation (and subsequent olefin isomerization) of methylene-linked γ-alkynylaldehydes: Takeishi, K.; Sugishima, K.; Sasaki, K.; Tanaka, K. Chem. Eur. J. 2004, 10, 5681.
    • (2004) Chem. Eur. J. , Issue.10 , pp. 5681
    • Takeishi, K.1    Sugishima, K.2    Sasaki, K.3    Tanaka, K.4
  • 49
    • 77349099246 scopus 로고    scopus 로고
    • Review of transition-metal-catalyzed hydroacylation: Willis, M. C. Chem. Rev. 2010, 110, 725.
    • (2010) Chem. Rev. , vol.110 , pp. 725
    • Willis, M.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.