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Volumn 10, Issue 18, 2008, Pages 4017-4020

Cyclization via carbolithiation of α-amino alkyllithium reagents

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBON; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LITHIUM;

EID: 55949088005     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801523r     Document Type: Article
Times cited : (32)

References (53)
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    • Review of synthetic work, (d) Liu, J.; Hsung, R. P. Chemtracts 2005, 18, 321-330.
    • (2005) Chemtracts , vol.18 , pp. 321-330
    • Liu, J.1    Hsung, R.P.2
  • 6
    • 33745698645 scopus 로고    scopus 로고
    • Review of synthetic work: b
    • Review of synthetic work: (b) Weinreb, S. M. Chem. Rev. 2006, 106, 2531-2549.
    • (2006) Chem. Rev , vol.106 , pp. 2531-2549
    • Weinreb, S.M.1
  • 11
    • 11044222000 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see: Fleming, F. F.; Zhang, Z. Tetrahedron 2005, 61, 747-789.
    • (2005) Tetrahedron , vol.61 , pp. 747-789
    • Fleming, F.F.1    Zhang, Z.2
  • 30
    • 0000137721 scopus 로고    scopus 로고
    • Freeman's reagent: Freeman, P. K.; Hutchinson, L. L. Tetrahedron Lett. 1976, 17, 1849-1852.
    • Freeman's reagent: Freeman, P. K.; Hutchinson, L. L. Tetrahedron Lett. 1976, 17, 1849-1852.
  • 32
  • 33
    • 0000644216 scopus 로고    scopus 로고
    • Leading references: (c) Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064-1071.
    • Leading references: (c) Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064-1071.
  • 41
    • 61349106909 scopus 로고    scopus 로고
    • Only fully substituted α-aminonitrile compounds displayed a propensity to undergo a retro-Strecker reaction. To avoid decomposition, compounds were purified using basic aluminia flash chromatography and characterized in d6-benzene
    • 6-benzene.
  • 44
    • 61349090165 scopus 로고    scopus 로고
    • Details are provided in the Supporting Information section
    • Details are provided in the Supporting Information section.
  • 47
    • 33645037635 scopus 로고    scopus 로고
    • Alkyllithium intermediates deprotonating THF over extended periods of time, (a) Deng, K.; Bensari-Bouguerra, A.; Whetstone, J.; Cohen, T. J. Org. Chem. 2006, 71, 2360-2372.
    • Alkyllithium intermediates deprotonating THF over extended periods of time, (a) Deng, K.; Bensari-Bouguerra, A.; Whetstone, J.; Cohen, T. J. Org. Chem. 2006, 71, 2360-2372.
  • 52
    • 61349085174 scopus 로고    scopus 로고
    • Geometry optimizations were performed with B3LYP/6-31G* as implemented in Gaussian 03. Minima were characterized by their vibrational frequencies. The transition states were characterized by vibrational frequency calculations as well as internal reaction coordinate calculations. The energies reported are enthalpies without zero-point corrections. Transition state geometries and the full Gaussian 03 reference is included in the Supporting Information section.
    • Geometry optimizations were performed with B3LYP/6-31G* as implemented in Gaussian 03. Minima were characterized by their vibrational frequencies. The transition states were characterized by vibrational frequency calculations as well as internal reaction coordinate calculations. The energies reported are enthalpies without zero-point corrections. Transition state geometries and the full Gaussian 03 reference is included in the Supporting Information section.
  • 53
    • 61349131062 scopus 로고    scopus 로고
    • The relative energy between the two transition states in Figure 1 is unreasonably large, but the actual values are unlikely to be very accurate because of the complete neglect of solvation in these calculations.
    • The relative energy between the two transition states in Figure 1 is unreasonably large, but the actual values are unlikely to be very accurate because of the complete neglect of solvation in these calculations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.