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Volumn 130, Issue 7, 2008, Pages 2172-2173

A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; LIGAND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM; SULFOXIDE; TRANSITION ELEMENT;

EID: 39649093904     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710665q     Document Type: Article
Times cited : (143)

References (42)
  • 19
    • 0001425763 scopus 로고
    • For attempts showing low selectivities/reactivities: a
    • For attempts showing low selectivities/reactivities: (a) James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927.
    • (1977) Can. J. Chem , vol.55 , pp. 3927
    • James, B.R.1    McMillan, R.S.2
  • 22
    • 0027997952 scopus 로고
    • For somewhat better selectivities using sulfoxide/nitrogen or sulfoxide/phosphine chelates, see: a
    • For somewhat better selectivities using sulfoxide/nitrogen or sulfoxide/phosphine chelates, see: (a) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron Asymmetry 1994, 5, 1895.
    • (1994) Tetrahedron Asymmetry , vol.5 , pp. 1895
    • Allen, J.V.1    Bower, J.F.2    Williams, J.M.J.3
  • 28
    • 37049069973 scopus 로고
    • For Rh-catalysis with ligand systems that incorporate potentially ligating sulfoxide moieties, see: a
    • For Rh-catalysis with ligand systems that incorporate potentially ligating sulfoxide moieties, see: (a) Kvintovics, P.; James, B. R.; Heil, B. J. Chem. Soc., Chem. Commun. 1986, 1810.
    • (1986) J. Chem. Soc., Chem. Commun , pp. 1810
    • Kvintovics, P.1    James, B.R.2    Heil, B.3
  • 30
    • 0041738169 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
    • (2003) Chem. Rev , vol.103 , pp. 2829
    • Hayashi, T.1    Yamasaki, K.2
  • 33
    • 39649110477 scopus 로고    scopus 로고
    • Alternatively, the present sulfinate (S or R) can be obtained in high yield in one step: Solladie, G.; Hutt, J.; Girardin, A. Synthesis 1987, 67, 173.
    • Alternatively, the present sulfinate (S or R) can be obtained in high yield in one step: Solladie, G.; Hutt, J.; Girardin, A. Synthesis 1987, 67, 173.
  • 34
    • 1942532931 scopus 로고    scopus 로고
    • The synthesis of (M,S,S)-1 and (P,S,S)-1 has been reported: Clayden, J.; Kubinski, P. M.; Sammiceli, F.; Helliwell, M.; Diorazio, L. Tetrahedron 2004, 60, 4387.
    • The synthesis of (M,S,S)-1 and (P,S,S)-1 has been reported: Clayden, J.; Kubinski, P. M.; Sammiceli, F.; Helliwell, M.; Diorazio, L. Tetrahedron 2004, 60, 4387.
  • 35
    • 39649090831 scopus 로고    scopus 로고
    • Its enantiomer (M,S,S)-1 also reacts readily with the Rh precursor, whereas (M,R,R)-1 and (P,S,S)-1 do not react cleanly to give the corresponding complexes. In this case, the relative orientation of the tolyl groups on the sulfoxides hinder formation of the dimer.
    • Its enantiomer (M,S,S)-1 also reacts readily with the Rh precursor, whereas (M,R,R)-1 and (P,S,S)-1 do not react cleanly to give the corresponding complexes. In this case, the relative orientation of the tolyl groups on the sulfoxides hinder formation of the dimer.
  • 38
    • 0001257694 scopus 로고    scopus 로고
    • For comparative studies on the binding ability of sulfoxides to LTMs: (a) Pettinari, C.; Pellei, M.; Caviccio, G.; Crucianelli, M.; Panzeri, W.; Colapietro, M.; Cassetta, A. Organometallics 1999, 18, 555.
    • For comparative studies on the binding ability of sulfoxides to LTMs: (a) Pettinari, C.; Pellei, M.; Caviccio, G.; Crucianelli, M.; Panzeri, W.; Colapietro, M.; Cassetta, A. Organometallics 1999, 18, 555.
  • 42
    • 39649116130 scopus 로고    scopus 로고
    • Whether epimerization of the methyl group occurs during catalysis under the reaction conditions used is not clear at this stage
    • (b) Whether epimerization of the methyl group occurs during catalysis under the reaction conditions used is not clear at this stage.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.