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Volumn , Issue 3, 2006, Pages 440-444

Practical and efficient synthesis of (E)-α,β-unsaturated amides bearing (S)-α-methylbenzylamine from 2-phosphonamides via Horner-Wadsworth-Emmons reaction

Author keywords

, unsaturated amides; (S) methylbenzylamine; Chiral phosphonamides; Horner Wadsworth Emmons reaction

Indexed keywords

2 PHOSPHONAMIDE DERIVATIVE; ALPHA METHYLBENZYLAMINE; AMIDE; UNCLASSIFIED DRUG;

EID: 33344476694     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926265     Document Type: Article
Times cited : (18)

References (36)
  • 18
    • 0001261089 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford
    • (b) Kelly, S. E. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 755.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 755
    • Kelly, S.E.1
  • 19
    • 0036216970 scopus 로고    scopus 로고
    • For an asymmetric version of the HWE reaction, see: (a) Rein, T.; Pedersen, T. M. Synthesis 2002, 579.
    • (2002) Synthesis , pp. 579
    • Rein, T.1    Pedersen, T.M.2
  • 26
    • 0028888483 scopus 로고
    • The non-chiral diethoxyphosphoryl-N-(1-methylbenzyl)acetamide has been obtained from diethoxyphosphorylacetyl chloride and 1 -methylbenzylamine and used in the preparation of (E)-N-(1-methylbenzyl)-4-phenyl-2-butenamide via the HWE reaction: Janecki, T.; Bodalski, R.; Wieczorek, M.; Bujacz, G. Tetrahedron 1995, 51, 1721.
    • (1995) Tetrahedron , vol.51 , pp. 1721
    • Janecki, T.1    Bodalski, R.2    Wieczorek, M.3    Bujacz, G.4
  • 28
    • 0034725908 scopus 로고    scopus 로고
    • Similar HWE reactions using NaI, NaBr, and KI in the presence of DBU have been reported: Ando, K. J. Org. Chem. 2000, 65, 4745.
    • (2000) J. Org. Chem. , vol.65 , pp. 4745
    • Ando, K.1
  • 29
    • 33344461739 scopus 로고    scopus 로고
    • note
    • The E and Z isomers for 5d and 5e were easily separable by flash chromatography.
  • 30
    • 33344460775 scopus 로고    scopus 로고
    • note
    • When the minor diastereomer was not detected, an E/Z ratio 98:02 is shown in Tables 1 and 3.
  • 31
    • 33344461861 scopus 로고    scopus 로고
    • note
    • The coupling constant between the olefinic protons of compound 5a-f was J = 15 Hz for E and J = 11 Hz for Z; this is in agreement with the average literature values.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.