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Volumn 126, Issue 3, 2005, Pages 377-383

Asymmetric synthesis of α-monofluoromethyl- and α- difluoromethylbenzylamines through regioselective hydrogenolysis

Author keywords

Asymmetric synthesis; Diastereomerically pure bis( methylbenzyl)amine derivative; Partially fluorinated methyl group; Regioselective hydrogenolysis; Difluoromethylbenzylamine; Monofluoromethylbenzylamine

Indexed keywords

ACETOPHENONE; ALPHA METHYLBENZYLAMINE; AMINE; BENZYLAMINE DERIVATIVE; METHYL GROUP;

EID: 15944370582     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.01.009     Document Type: Article
Times cited : (14)

References (17)
  • 5
    • 0035819654 scopus 로고    scopus 로고
    • Only novel synthesis of racemic α-difluoromethylbenzylamine derivatives has been reported, B. Greedy, and V. Gouverneur Chem. Commun. 2001 233 234
    • (2001) Chem. Commun. , pp. 233-234
    • Greedy, B.1    Gouverneur, V.2
  • 7
    • 15944417594 scopus 로고    scopus 로고
    • note
    • Rotation frame nuclear Overhauser Effect.
  • 8
    • 85102983882 scopus 로고    scopus 로고
    • note
    • 4Si], δ 1.54 (d, 6.4 Hz, 3H), 2.26 (s, 3H), 4.84 (q, 6.4 Hz, 1H), 7.10-7.90 (Ar-H, 10H).
  • 10
    • 0242523155 scopus 로고    scopus 로고
    • 3-2 has been reported to be Z configuration, which is inconsistent with our result (E configuration), B. Torok, and G.K.S. Prakash Adv. Synth. Catal. 345 2003 165 168
    • (2003) Adv. Synth. Catal. , vol.345 , pp. 165-168
    • Torok, B.1    Prakash, G.K.S.2
  • 11
    • 85102984393 scopus 로고    scopus 로고
    • note
    • 1-3 was calculated to be S,S:R,S = 64:36 (found 67:33).
  • 12
    • 85102984186 scopus 로고    scopus 로고
    • note
    • 4Si], δ 1.27 (d, 6.6 Hz, 6H), 1.60 (br, 1H), 3.50 (q, 6.6 Hz, 2H), 7.18-7.35 (Ar-H, 10H).
  • 14
    • 15944398069 scopus 로고    scopus 로고
    • note
    • 4Si], δ 24.18, 36.31, 48.77, 58.06, 125.95, 126.40, 126.73, 128.27, 128.55, 139.94, 145.48.
  • 15
    • 0032506575 scopus 로고    scopus 로고
    • (D)-phenylalanine derivatives were prepared through cis-2,3-disubstituted aziridines, which was synthesized from N-α-hydroxymethylbenzyl-α- methylbenzylamines via intramolecular cyclization, by the same regioselective manner as our case, J.-W. Chang, J.H. Bae, S.-H. Shin, C.S. Park, D. Choi, and W.K. Lee Tetrahedron Lett. 39 1998 9193 9196
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9193-9196
    • Chang, J.-W.1    Bae, J.H.2    Shin, S.-H.3    Park, C.S.4    Choi, D.5    Lee, W.K.6
  • 17
    • 15944411450 scopus 로고
    • Fluorine would most closely resemble and mimic hydrogen with respect to steric requirement
    • R.E. Banks (Ed.), Ellis Horwood Ltd., Chichester, UK, (Chapter 6).
    • Fluorine would most closely resemble and mimic hydrogen with respect to steric requirement, R. Filler, in: R.E. Banks (Ed.), Organofluorine Chemicals and Their Industrial Applications, Ellis Horwood Ltd., Chichester, UK, 1979 (Chapter 6).
    • (1979) Organofluorine Chemicals and Their Industrial Applications
    • Filler, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.