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Volumn 131, Issue 26, 2009, Pages 9178-9179

Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST LOADINGS; CHEMICAL EQUATIONS; CYCLOBUTANONES; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; LARGE SCALE SYNTHESIS; PRODUCT FORMATION; RING EXPANSION; STEREOGENIC CENTERS; UNSATURATED ESTERS;

EID: 67649976797     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904055z     Document Type: Article
Times cited : (199)

References (39)
  • 1
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    • For general reviews of the chemistry of cyclobutanes, see: a
    • For general reviews of the chemistry of cyclobutanes, see: (a) Belluš, D.; Ernst, B. Angew. Chem. 1988, 100, 820.
    • (1988) Angew. Chem , vol.100 , pp. 820
    • Belluš, D.1    Ernst, B.2
  • 4
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    • Rappoport, Z, Liebman, J. F, Eds, John Wiley & Sons: Chichester, U.K
    • Lee-Ruff, E. In The Chemistry of Cyclobutanes; Rappoport, Z., Liebman, J. F., Eds.; John Wiley & Sons: Chichester, U.K., 2005.
    • (2005) The Chemistry of Cyclobutanes
    • Lee-Ruff, E.1
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    • Cyclobutanones: (a) Trost, B. M.; Yasukata, T. J. Am. Chem. Soc. 2001, 123, 7162.
    • Cyclobutanones: (a) Trost, B. M.; Yasukata, T. J. Am. Chem. Soc. 2001, 123, 7162.
  • 12
    • 33646579577 scopus 로고    scopus 로고
    • Cyclopentanones: (b) Trost, B. M.; Xie, J. J. Am. Chem. Soc. 2006, 128, 6044.
    • Cyclopentanones: (b) Trost, B. M.; Xie, J. J. Am. Chem. Soc. 2006, 128, 6044.
  • 14
    • 0000787875 scopus 로고    scopus 로고
    • For an alternative entry to chiral cyclobutanones based on a Wagner-Meerwein shift induced by a Sharpless asymmetric epoxidation, see: (d) Nemoto, H, Ishibashi, H, Nagamochi, M, Fukumoto, K. J. Org. Chem. 1992, 57, 1707
    • For an alternative entry to chiral cyclobutanones based on a Wagner-Meerwein shift induced by a Sharpless asymmetric epoxidation, see: (d) Nemoto, H.; Ishibashi, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1992, 57, 1707.
  • 15
    • 33846207883 scopus 로고    scopus 로고
    • For recent general reviews of gold catalysis, see: a
    • For recent general reviews of gold catalysis, see: (a) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
    • (2007) Chem. Commun , pp. 333
    • Jiménez-Núñez, E.1    Echavarren, A.M.2
  • 23
    • 67749106304 scopus 로고    scopus 로고
    • For a ruthenium-catalyzed version of the same ring expansion reaction, see: b
    • For a ruthenium-catalyzed version of the same ring expansion reaction, see: (b) Trost, B. M.; Xie, J.; Maulide, N. J. Am. Chem. Soc. 2008, 130, 17258.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 17258
    • Trost, B.M.1    Xie, J.2    Maulide, N.3
  • 24
    • 53849089263 scopus 로고    scopus 로고
    • and references therein. For a review of 1,2-alkyl migrations catalyzed by π acids, see
    • For a review of 1,2-alkyl migrations catalyzed by π acids, see: Crone, B.; Kirsch, S. F Chem. - Eur. J. 2008, 14, 3514, and references therein.
    • (2008) Chem. - Eur. J , vol.14 , pp. 3514
    • Crone, B.1    Kirsch, S.F.2
  • 25
    • 0032473509 scopus 로고    scopus 로고
    • For reviews of catalytic enantioselective formation of quaternary stereocenters, see: a
    • For reviews of catalytic enantioselective formation of quaternary stereocenters, see: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
    • (1998) Angew. Chem., Int. Ed , vol.37 , pp. 388
    • Corey, E.J.1    Guzman-Perez, A.2
  • 28
    • 67649970248 scopus 로고    scopus 로고
    • For all three major bisphosphine ligand families BINAP, BIPHEP, and Segphos, the same trend was observed, with the xylyl-substituted representatives providing the highest selectivity within each family
    • For all three major bisphosphine ligand families (BINAP, BIPHEP, and Segphos), the same trend was observed, with the xylyl-substituted representatives providing the highest selectivity within each family.
  • 29
    • 67649976309 scopus 로고    scopus 로고
    • 4, AgOTf, and AgOTs led to formation of 2 in only 67, 34, and 15% ee, respectively.
    • 4, AgOTf, and AgOTs led to formation of 2 in only 67, 34, and 15% ee, respectively.
  • 30
    • 67649973331 scopus 로고    scopus 로고
    • AgNTf2 was found to slowly catalyze the ring expansion of 1, These observations suggest that the achiral catalyst causing the background reaction was not the silver cation
    • 2. These observations suggest that the achiral catalyst causing the background reaction was not the silver cation.
    • 2
  • 31
    • 34249978190 scopus 로고    scopus 로고
    • As opposed to 1,1-disubstituted allenes, for which intramolecular addition of the alcohol onto the allene was never observed, tri- and tetrasubstituted allenes generated substantial amounts of dihydrofuran byproducts. For an example of formation of dihydrofurans from alkoxyallenes, see: Yeom, H.-S.; Yoon, S.-J.; Shin, S. Tetrahedron Lett. 2007, 48, 4817.
    • As opposed to 1,1-disubstituted allenes, for which intramolecular addition of the alcohol onto the allene was never observed, tri- and tetrasubstituted allenes generated substantial amounts of dihydrofuran byproducts. For an example of formation of dihydrofurans from alkoxyallenes, see: Yeom, H.-S.; Yoon, S.-J.; Shin, S. Tetrahedron Lett. 2007, 48, 4817.
  • 32
    • 67649973332 scopus 로고    scopus 로고
    • The absolute configuration of cyclobutanone 4 was determined by crystal structure analysis of the corresponding tosylhydrazone. The absolute configurations of compounds 2 and 9 were assigned by comparison of the optical rotation with reported values see ref 4a, The absolute configurations of all the other compounds were assigned by analogy
    • The absolute configuration of cyclobutanone 4 was determined by crystal structure analysis of the corresponding tosylhydrazone. The absolute configurations of compounds 2 and 9 were assigned by comparison of the optical rotation with reported values (see ref 4a). The absolute configurations of all the other compounds were assigned by analogy.
  • 34
    • 35349012652 scopus 로고    scopus 로고
    • For examples of gold-catalyzed enantioselective reactions of allenes, see: (a) Luzung, M. R, Mauleón, P, Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402
    • For examples of gold-catalyzed enantioselective reactions of allenes, see: (a) Luzung, M. R.; Mauleón, P.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.