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Volumn 129, Issue 12, 2007, Pages 3470-3471

An unexpected role of a trace amount of water in catalyzing proton transfer in phosphine-catalyzed (3 + 2) cycloaddition of allenoates and alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; DEUTERIUM; PHOSPHINE; WATER;

EID: 33947614581     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068215h     Document Type: Article
Times cited : (419)

References (34)
  • 2
    • 0034867881 scopus 로고    scopus 로고
    • For reviews on phosphine catalyzed reactions, see: a
    • For reviews on phosphine catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
    • (2001) Acc. Chem. Res , vol.34 , pp. 535
    • Lu, X.1    Zhang, C.2    Xu, Z.3
  • 19
    • 0037136118 scopus 로고    scopus 로고
    • Only a few computational studies have been done to rationalize the regiochemistry in the (3 + 2) cycloaddition step shown in Scheme 1, see: (a) Pham, T. Q.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron Lett. 2002, 43, 5953.
    • Only a few computational studies have been done to rationalize the regiochemistry in the (3 + 2) cycloaddition step shown in Scheme 1, see: (a) Pham, T. Q.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron Lett. 2002, 43, 5953.
  • 22
    • 4143094833 scopus 로고    scopus 로고
    • For a recent thematic issue on organocatalysis, see:, and references therein
    • For a recent thematic issue on organocatalysis, see: Houk, K. N.; List, B. Acc. Chem. Rev. 2004, 137, 487 and references therein.
    • (2004) Acc. Chem. Rev , vol.137 , pp. 487
    • Houk, K.N.1    List, B.2
  • 23
    • 33947672637 scopus 로고    scopus 로고
    • sol values are somehow overestimated (owing to the overestimation of the entropy contributions in solution), the main purpose of such calculations is to appreciate how solvent influences a reaction (such as on its reaction rate, regio- and stereochemistry). A discussion of regiochemistry is given in the Supporting Information.
    • sol values are somehow overestimated (owing to the overestimation of the entropy contributions in solution), the main purpose of such calculations is to appreciate how solvent influences a reaction (such as on its reaction rate, regio- and stereochemistry). A discussion of regiochemistry is given in the Supporting Information.
  • 24
    • 33947661167 scopus 로고    scopus 로고
    • Calculations showed that tunneling effect for this step is negligible.9
    • 9
  • 25
    • 33947623403 scopus 로고    scopus 로고
    • 3. For details of these and other experiments, see the Supporting Information.
    • 3. For details of these and other experiments, see the Supporting Information.
  • 26
    • 1842450590 scopus 로고    scopus 로고
    • [1,2] or [1,3] proton shift is proposed in many phosphine catalyzed reactions: (a) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118.
    • [1,2] or [1,3] proton shift is proposed in many phosphine catalyzed reactions: (a) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118.
  • 32
    • 33748898492 scopus 로고    scopus 로고
    • Such water-assisted proton shifts have been found in many enzymatic reactions, for a recent review, see:, and references therein
    • Such water-assisted proton shifts have been found in many enzymatic reactions, for a recent review, see: Blomberg, M. R. A.; Siegbahn, P. E. M. Biochim. Biophys. Acta 2006, 1757, 969 and references therein.
    • (2006) Biochim. Biophys. Acta , vol.1757 , pp. 969
    • Blomberg, M.R.A.1    Siegbahn, P.E.M.2
  • 34
    • 33845788846 scopus 로고    scopus 로고
    • Int. Ed, and references therein
    • (b) Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 8103 and references therein.
    • (2006) Angew. Chem , vol.45 , pp. 8103
    • Hayashi, Y.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.