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Volumn 130, Issue 46, 2008, Pages 15688-15701

Diastereoselective addition of zincated hydrazones to alkenylboronates and stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; BORON; CARBON; CHEMICAL BONDS; CONDENSATION REACTIONS; DENSITY FUNCTIONAL THEORY; KETONES; STEREOSELECTIVITY; ZINC;

EID: 56449117142     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806258v     Document Type: Article
Times cited : (26)

References (53)
  • 15
    • 7744225108 scopus 로고    scopus 로고
    • Preliminary communication: (a) Nakamura, M.; Hatakeyama, T.; Hara, K.; Fukudome, H.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 14344-14345.
    • Preliminary communication: (a) Nakamura, M.; Hatakeyama, T.; Hara, K.; Fukudome, H.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 14344-14345.
  • 16
    • 56449117117 scopus 로고    scopus 로고
    • When we used LDA in THF for deprotonation, the subsequent addition reaction was very slow. We assume that the diisopropylamine or THF slowed down the addition reaction through coordination to the zinc atom
    • When we used LDA in THF for deprotonation, the subsequent addition reaction was very slow. We assume that the diisopropylamine or THF slowed down the addition reaction through coordination to the zinc atom.
  • 17
    • 0000450307 scopus 로고    scopus 로고
    • The X-ray structure of the lithiated hydrazone has been reported (s- trans, as in SM6 in Figure 8). See: Collum, D. B.; Kahne, D.; Gut, S. A.; Depue, R. T.; Mohamadi, F.; Wanat, R. A.; Clardy, J.; Duyne, G. V. J. Am. Chem. Soc. 1984, 106, 4865-4869.
    • The X-ray structure of the lithiated hydrazone has been reported (s- trans, as in SM6 in Figure 8). See: Collum, D. B.; Kahne, D.; Gut, S. A.; Depue, R. T.; Mohamadi, F.; Wanat, R. A.; Clardy, J.; Duyne, G. V. J. Am. Chem. Soc. 1984, 106, 4865-4869.
  • 18
    • 85102093305 scopus 로고    scopus 로고
    • The rate of the addition reaction increased in the order THF < Et 2O < hexane. We assume that coordinative solvents prevent π-complex formation between the zincated hydrazone and alkenylboronates, such as in CP3 and CP4 in Figure 8
    • 2O < hexane. We assume that coordinative solvents prevent π-complex formation between the zincated hydrazone and alkenylboronates, such as in CP3 and CP4 in Figure 8.
  • 27
    • 0001969676 scopus 로고
    • Enders, D. Chem. Scr. 1985, 25, 139-147.
    • (1985) Chem. Scr , vol.25 , pp. 139-147
    • Enders, D.1
  • 33
    • 56449115174 scopus 로고    scopus 로고
    • CP1 is 1.8 kcal/mol lower in total electronic energy than SM1 + ethylene.
    • CP1 is 1.8 kcal/mol lower in total electronic energy than SM1 + ethylene.
  • 34
    • 56449108099 scopus 로고    scopus 로고
    • CP2 is 1.1 kcal/mol lower in total electronic energy than SM2 + ethylene.
    • CP2 is 1.1 kcal/mol lower in total electronic energy than SM2 + ethylene.
  • 41
    • 56449093408 scopus 로고    scopus 로고
    • For MO analyses of organozinc reactions using localized molecular orbital (LMO) and natural bond orbital (NBO) methods, see: (a) Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2804.
    • For MO analyses of organozinc reactions using localized molecular orbital (LMO) and natural bond orbital (NBO) methods, see: (a) Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2804.
  • 44
    • 56449083993 scopus 로고    scopus 로고
    • We used the heptane polarity for the PCM calculation. The relative energies of TSA2-TSD2 obtained from the PCM calculation (B3LYP/631A) are 0, 2.37, 1.38, and 2.76 kcal/mol, respectively
    • We used the heptane polarity for the PCM calculation. The relative energies of TSA2-TSD2 obtained from the PCM calculation (B3LYP/631A) are 0, 2.37, 1.38, and 2.76 kcal/mol, respectively.
  • 46
    • 56449103469 scopus 로고    scopus 로고
    • Gaussian, Inc, Pittsburgh, PA
    • Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Pittsburgh, PA, 2003.
    • (2003) Gaussian 03, revision , Issue.C.02
    • Frisch, M.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.