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Volumn 58, Issue 2, 2010, Pages 265-269

Stereoselective radical addition of an acetal to sterically tuned enantiomerically pure N-sulfinyl imines

Author keywords

Asymmetric synthesis; Dimethylzinc; Radical reaction; Sulfonamide

Indexed keywords

ACETAL; AMINE; AMINOALCOHOL; BORON; BORON TRIFLUORIDE DIETHYL ETHERATE; IMINE; N BENZYLIDENE 4 TOLUENESULFINAMIDE; N SULFINYL IMINES; SULFINAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 76249094972     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.58.265     Document Type: Article
Times cited : (16)

References (43)
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    • Radicals in Organic Synthesis, ed. by Renaud P., Sibi M. P., Wiley-VCH, Weinhem, 2001.
    • "Radicals in Organic Synthesis", ed. by Renaud P., Sibi M. P., Wiley-VCH, Weinhem, 2001.
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    • Radicals in Synthesis I & II, ed. by Gansäuer A., Springer-Verlag, Berlin, Heidelberg, 2006.
    • "Radicals in Synthesis I & II," ed. by Gansäuer A., Springer-Verlag, Berlin, Heidelberg, 2006.
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    • Acetal 2 was prepared according to reported procedure, see: Willy W. E., Binsch G., Eliel E. L., J. Am. Chem. Soc., 92, 5394-5402 (1970).
    • Acetal 2 was prepared according to reported procedure, see: Willy W. E., Binsch G., Eliel E. L., J. Am. Chem. Soc., 92, 5394-5402 (1970).
  • 27
    • 62149138331 scopus 로고    scopus 로고
    • A mild and robust method for cleaving sulfonamides was reported during the preparation of this manuscript: Ankner T., Hilmersson G., Org. Lett., 11, 503-506 (2009).
    • A mild and robust method for cleaving sulfonamides was reported during the preparation of this manuscript: Ankner T., Hilmersson G., Org. Lett., 11, 503-506 (2009).
  • 30
    • 76249097120 scopus 로고    scopus 로고
    • The final geometry optimization was performed using Gaussian 03W: Gaussian, Inc., Wallingford CT, 2004, for initial geometries generated by the conformational search using Spartan '06: Wavefunction, Inc. Irvine, CA. All the ground states were verified by vibrational frequency analysis.
    • The final geometry optimization was performed using Gaussian 03W: Gaussian, Inc., Wallingford CT, 2004, for initial geometries generated by the conformational search using Spartan '06: Wavefunction, Inc. Irvine, CA. All the ground states were verified by vibrational frequency analysis.
  • 36
    • 76249097374 scopus 로고    scopus 로고
    • Another possibility might be a reverse reaction due to lesser stability or a slower reaction with dimethylzinc of the sterically hindered intermediate aminyl radical derived from 5
    • Another possibility might be a reverse reaction due to lesser stability or a slower reaction with dimethylzinc of the sterically hindered intermediate aminyl radical derived from 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.