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Volumn 87, Issue 12, 2009, Pages 1682-1691

Chemo- and regio-selective functionalization of Morita-Baylis-Hiliman bromides with anthranilic acid

Author keywords

Anthranilic acid; Morita Baylis Hillman reaction; Morita Baylis Hillrnan bromides; Nucleophilic substitution

Indexed keywords

ANTHRANILIC ACID; CHEMOSELECTIVE; FUNCTIONALIZED; MORITA-BAYLIS-HILLMAN ADDUCTS; MORITA-BAYLIS-HILLMAN REACTION; NUCLEOPHILIC SUBSTITUTIONS; REGIO-SELECTIVE; SYNTHONS;

EID: 72549085702     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V09-128     Document Type: Article
Times cited : (1)

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    • It is well-documented in the literature that β vinylic proton cis to ester appear downfield when compared to trans β vinylic proton: see for example: Jackman, L. M.; Sternhell, S. Applications of nuclear magnetic resonance spectroscopyin organic chemistry, 2nd ed; Pergamon: Oxford, 1969; Vol.5
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    • It is reported that β vinylic proton cis and trans to ester resonate at ̃ δ 7.5 and δ 6.5, respectively. The vinylic protons of compounds 3a 3d, 4a, 4b, 5a, and 5b were observed at δ 7.76-8.11 ppm. Thus, E stereochemistry was assigned to these compounds: Tobey, S. W. J. Org. Chem. 1969, 34 (5), 1281-1298. doi:10.1021/jo01257a019.
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    • Kim, J.N.1    Chung, Y.M.2    Im, Y.J.3
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    • Synthesis of ethyl 3-cyano-2-methylcinnamates and 3-cyano-2- methylcinnamonitriles from the Baylis-Hillman acetates
    • DOI 10.1016/S0040-4039(01)01971-2, PII S0040403901019712
    • Chung, Y. M.; Gong, J. H.; Kim, T. H.; Kim, J. N. Tetrahe(Iron Lett. 2001, 42 (51), 9023-9026. doi:10.1016/S0040-4039(01)0 1971-2. (Pubitemid 33145159)
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    • Chung, Y.M.1    Gong, J.H.2    Kim, T.H.3    Kim, J.N.4


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