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Volumn 132, Issue 39, 2010, Pages 13600-13603

Enantioselective α-benzylation of aldehydes via photoredox organocatalysis

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS; BENZYLATION; DRUG TARGETS; ELECTRON-DEFICIENT; ENANTIOSELECTIVE; FLUORESCENT LIGHT; ORGANOCATALYSIS; ORGANOCATALYSTS;

EID: 77957304088     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106593m     Document Type: Article
Times cited : (465)

References (37)
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    • The racemic homolytic alkylation of stoichiometric enamines using p -nitrobenzyl chloride as radical precursor is known; see
    • The racemic homolytic alkylation of stoichiometric enamines using p -nitrobenzyl chloride as radical precursor is known; see: Russell, G. A. and Wang, K. J. Org. Chem. 1991, 56, 3475
    • (1991) J. Org. Chem. , vol.56 , pp. 3475
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    • 3CN) and the nucleophilic nature of the unsubstituted benzylic radical. For benzyl bromide reduction potential, see:, For benzylic radical nucleophilicity, see:, Org. Lett. 2007, 9, 2721
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    • (1987) J. Electrochem. Soc. , vol.134 , pp. 3062
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    • DFT calculations were performed with the use of B3LYP/6-311+G(2d,2p)// B3LYP/6-31G(d)
    • DFT calculations were performed with the use of B3LYP/6-311+G(2d,2p)// B3LYP/6-31G(d).
  • 32
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    • 2 is a competent photoredox catalyst for these transformations but usually results in lower conversion; for photophysical properties, see
    • 2 is a competent photoredox catalyst for these transformations but usually results in lower conversion; for photophysical properties, see: Kalyanasundaram, K. Coord. Chem. Rev. 1982, 46, 159
    • (1982) Coord. Chem. Rev. , vol.46 , pp. 159
    • Kalyanasundaram, K.1
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    • a values in DMSO, see:, For reduction potentials, see: J. Am. Chem. Soc. 1970, 92, 7154
    • a values in DMSO, see: Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456 For reduction potentials, see: Wiberg, K. B. and Lewis, T. P. J. Am. Chem. Soc. 1970, 92, 7154
    • (1988) Acc. Chem. Res. , vol.21 , pp. 456
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    • The parent bromomethyl-heterocycles lacking additional substitution (e.g., 2-(bromomethyl)pyrazine) are reported to be unstable; for pyrimidines, see:, For pyrazines, see:, Org. Biomol. Chem. 2004, 2, 2852 For triazines, see: Sci. Synth. 2003, 17, 449
    • The parent bromomethyl-heterocycles lacking additional substitution (e.g., 2-(bromomethyl)pyrazine) are reported to be unstable; for pyrimidines, see: Brown, D. J. and Waring, P. Aust. J. Chem. 1974, 27, 2251 For pyrazines, see: Sasaki, K., Sugou, K., Miyamoto, K., Hirai, J., Tsubouchi, S., Miyasaka, H., Itaya, A., and Kuroda, Y. Org. Biomol. Chem. 2004, 2, 2852 For triazines, see: Von Angerer, S. Sci. Synth. 2003, 17, 449
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.