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Volumn 64, Issue 24, 1999, Pages 8846-8854

Stereoselective synthesis of trifluoromethylated compounds: Nucleophilic addition of formaldehyde N,N-dialkylhydrazones to trifluoromethyl ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; FLUOROFORM; FORMALDEHYDE; HYDRAZONE DERIVATIVE; KETONE DERIVATIVE; PYRROLIDINE DERIVATIVE; REAGENT;

EID: 0345148379     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991049u     Document Type: Article
Times cited : (51)

References (62)
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    • Recents examples: (a) Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G. K. S.; Olah, G. A Angew. Chem., Int. Ed. Engl. 1998, 37, 820. (b) Walter, M. W.; Adlington, R. M.; Baldwin, J. E.; Schofield C. J. J. Org. Chem. 1998, 63, 5179. Yokohama, Y.; Mochida K. Synlett 1997, 907. Reviews: Begué, J.-P.; Bonnet-Delpon, D. Tetrahedron 1991, 47, 3207. (e) McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555.
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    • Recents examples: (a) Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G. K. S.; Olah, G. A Angew. Chem., Int. Ed. Engl. 1998, 37, 820. (b) Walter, M. W.; Adlington, R. M.; Baldwin, J. E.; Schofield C. J. J. Org. Chem. 1998, 63, 5179. Yokohama, Y.; Mochida K. Synlett 1997, 907. Reviews: Begué, J.-P.; Bonnet-Delpon, D. Tetrahedron 1991, 47, 3207. (e) McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555.
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    • note
    • Compound 7 is commercially available from Merck-Schuchardt, Hohenbrunn, Germany.
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    • note
    • 2O for the reaction of 3b and 10 resulted in the isolation of (S)-6b (R = Bn, NR′R″ = 2-(diphenylmethoxymethyl)pyrrolidine) in 22% yield, together with only 66% yield of the expected adduct 14d.
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    • Obtained from the parent known hydrazine (Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103) by condensation with paraformaldehyde: Díez, E.; Martín-Zamora, E.; Ferrete, A.; Fernández, R.; Lassaletta, J. M., unpublished results.
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    • unpublished results
    • Obtained from the parent known hydrazine (Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103) by condensation with paraformaldehyde: Díez, E.; Martín-Zamora, E.; Ferrete, A.; Fernández, R.; Lassaletta, J. M., unpublished results.
    • Díez, E.1    Martín-Zamora, E.2    Ferrete, A.3    Fernández, R.4    Lassaletta, J.M.5
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    • Very recently, two different groups have independently reported on the cleavage of N,N-dimethylhydrazones into nitriles using this system: (a) Stankovic, S.; Espenson, J. H. Chem. Commun. 1998, 1579. (b) Rudler, H.; Denise, B. Chem. Commun. 1998, 2145.
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    • Very recently, two different groups have independently reported on the cleavage of N,N-dimethylhydrazones into nitriles using this system: (a) Stankovic, S.; Espenson, J. H. Chem. Commun. 1998, 1579. (b) Rudler, H.; Denise, B. Chem. Commun. 1998, 2145.
    • (1998) Chem. Commun. , pp. 2145
    • Rudler, H.1    Denise, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.