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Volumn 133, Issue 24, 2011, Pages 9343-9353

Erratum: Density functional theory study of the mechanism and origins of stereoselectivity in the asymmetric simmons-smith cyclopropanation with charette chiral dioxaborolane ligand (Journal of the American Chemical Society (2011) 133 (9343-9353) DOI: 10.1021/ja111330z);Density functional theory study of the mechanism and origins of stereoselectivity in the asymmetric simmons-smith cyclopropanation with charette chiral dioxaborolane ligand

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATION THEORY; DIMERS; LIGANDS; PROPANE; STEREOSELECTIVITY; ZINC COMPOUNDS;

EID: 79959190293     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205871t     Document Type: Erratum
Times cited : (35)

References (106)
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    • revision C.02; Gaussian, Inc.: Wallingford, CT
    • Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 78
    • 79959266828 scopus 로고    scopus 로고
    • For the comparison of different basis sets, see the Supporting Information
    • For the comparison of different basis sets, see the Supporting Information.
  • 82
    • 79959213884 scopus 로고    scopus 로고
    • The UAKS radii are also tested, and the results are very similar to those with UA0 radii. For details, see the Supporting Information
    • The UAKS radii are also tested, and the results are very similar to those with UA0 radii. For details, see the Supporting Information.
  • 86
    • 0029945485 scopus 로고    scopus 로고
    • Davies and co-workers reported that, in the chiral Rh(II) complex-catalyzed cyclopropanation and related reactions, the steric repulsion factors are crucial for the enantioselectivity, see
    • Davies and co-workers reported that, in the chiral Rh(II) complex-catalyzed cyclopropanation and related reactions, the steric repulsion factors are crucial for the enantioselectivity, see: Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6897
    • Davies, H.M.L.1    Bruzinski, P.R.2    Lake, D.H.3    Kong, N.4    Fall, M.J.5
  • 106
    • 79959254271 scopus 로고    scopus 로고
    • The cyclopropanation of homoallylic alcohols gives the same absolute stereochemistry as that obtained with allylic alcohols. However, the enantiofacial selection in the Sharpless epoxidation of homoallylic alcohols is opposite to that observed for allylic alcohols (see ref 26a). Corey proposed that in the Sharpless epoxidation of homoallylic alcohols, the C4-C3-C5-C6 moiety of the homoallylic alcohol chain in the energetically favored transition state adopts an s - cis conformation due to the hydrogen bonding (see ref 26b)
    • The cyclopropanation of homoallylic alcohols gives the same absolute stereochemistry as that obtained with allylic alcohols. However, the enantiofacial selection in the Sharpless epoxidation of homoallylic alcohols is opposite to that observed for allylic alcohols (see ref 26a). Corey proposed that in the Sharpless epoxidation of homoallylic alcohols, the C4-C3-C5-C6 moiety of the homoallylic alcohol chain in the energetically favored transition state adopts an s-cis conformation due to the hydrogen bonding (see ref 26b).


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