메뉴 건너뛰기




Volumn 18, Issue 20, 2007, Pages 2427-2436

A convenient method for the preparation of chiral phosphonoacetamides and their Horner-Wadsworth-Emmons reaction

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 DIETHOXYPHOSPHORYL)ACETAMIDE 2 PHENYLETHANOL; 2 (2 DIMETHOXYPHOSPHORYL)ACETAMIDE 2 PHENYLETHANOL; 2 (DIMETHOXYPHOSPHORYLACETYL) (ALPHA METHYLBENZYL)BENZYLAMINE; 2 (DIMETHOXYPHOSPHORYLACETYL)BIS(ALPHA METHYLBENZYL)AMINE; ACETAMIDE DERIVATIVE; METHYL 2 [2 (DIMETHOXYPHOSPHORYL)ACETAMIDE] 2 PHENYLACETATE; METHYL N (3 ISO BUTYLACRYLOYL) 2 AMINO 2 PHENYLACETATE; METHYL N (3 ISO PROPYLACRYLOYL) 2 AMINO 2 PHENYLACETATE; METHYL N (3 TERT BUTYLACRYLOYL) 2 AMINO 2 PHENYLACETATE; METHYL N (4 CHLOROCINNAMOYL) 2 AMINO 2 PHENYLACETATE; METHYL N (4 METHOXYCINNAMOYL) 2 AMINO 2 PHENYLACETATE; METHYL N (CINNAMOYL) 2 AMINO 2 PHENYLACETATE; N (3 ISO BUTYLACRYLOYL) (ALPHA METHYLBENZYL)BENZYLAMINE; N (3 ISO BUTYLACRYLOYL) 2 AMINO 2 PHENYLETHANOL; N (3 ISO BUTYLACRYLOYL)BIS(ALPHA METHYLBENZYL)AMINE; N (3 ISO PROPYLACRYLOYL) (ALPHA METHYLBENZYL)BENZYLAMINE; N (3 ISO PROPYLACRYLOYL) 2 AMINO 2 PHENYLETHANOL; N (3 ISO PROPYLACRYLOYL)BIS(ALPHA METHYLBENZYL)AMINE; N (3 TERT BUTYLACRYLOYL) (ALPHA METHYLBENZYL)BENZYLAMINE; N (3 TERT BUTYLACRYLOYL) 2 AMINO 2 PHENYLETHANOL; N (3 TERT BUTYLACRYLOYL)BIS(ALPHA METHYLBENZYL)AMINE; N (4 CHLOROCINNAMOYL) (ALPHA METHYLBENZYL)BENZYLAMINE; N (4 CHLOROCINNAMOYL) 2 AMINO 2 PHENYLETHANOL; N (4 CHLOROCINNAMOYL)BIS(ALPHA METHYLBENZYL)AMINE; N (4 METHOXYCINNAMOYL) (ALPHA METHYLBENZYL)BENZYLAMINE; N (4 METHOXYCINNAMOYL) 2 AMINO 2 PHENYLETHANOL; N (4 METHOXYCINNAMOYL)BIS(ALPHA METHYLBENZYL)AMINE; N (CINNAMOYL) (ALPHA METHYLBENZYL)BENZYLAMINE; N (CINNAMOYL) 2 AMINO 2 PHENYLETHANOL; N (CINNAMOYL)BIS(ALPHA METHYLBENZYL)AMINE; UNCLASSIFIED DRUG;

EID: 35548993124     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.09.033     Document Type: Article
Times cited : (14)

References (98)
  • 5
    • 0000610534 scopus 로고
    • Helchem G., Hoffmann R.W., Mulzer J., and Schaumann E. (Eds), Thieme, Sttugart
    • Jurczak J., Bauer T., and Chapuis C. In: Helchem G., Hoffmann R.W., Mulzer J., and Schaumann E. (Eds). Stereoselective Synthesis (Houben-Weyl) Vol. E 21c (1995), Thieme, Sttugart 2735
    • (1995) Stereoselective Synthesis (Houben-Weyl) , vol.E 21c , pp. 2735
    • Jurczak, J.1    Bauer, T.2    Chapuis, C.3
  • 42
    • 0001848341 scopus 로고
    • For reviews on the HWE reaction, see:
    • For reviews on the HWE reaction, see:. Maryanoff B.E., and Reitz A.B. Chem. Rev. 89 (1989) 863-927
    • (1989) Chem. Rev. , vol.89 , pp. 863-927
    • Maryanoff, B.E.1    Reitz, A.B.2
  • 43
    • 0001071115 scopus 로고
    • Trost B.M., and Fleming I. (Eds), Pergamon Press, Oxford
    • Kelly S.E. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 1 (1991), Pergamon Press, Oxford 755
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 755
    • Kelly, S.E.1
  • 50
    • 0036216970 scopus 로고    scopus 로고
    • For asymmetric version of the HWE reaction, see:
    • For asymmetric version of the HWE reaction, see:. Rein T., and Pedersen T.M. Synthesis (2002) 579-594
    • (2002) Synthesis , pp. 579-594
    • Rein, T.1    Pedersen, T.M.2
  • 54
    • 0035808886 scopus 로고    scopus 로고
    • For the use of chiral α,β-unsaturated amides bearing (S)-(α-methylbenzyl)benzylamine as a Michael acceptor, see:
    • For the use of chiral α,β-unsaturated amides bearing (S)-(α-methylbenzyl)benzylamine as a Michael acceptor, see:. Castelot-Deliencourt G., Pannecoucke X., and Quirion J.C. Tetrahedron Lett. 42 (2001) 1025-1028
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1025-1028
    • Castelot-Deliencourt, G.1    Pannecoucke, X.2    Quirion, J.C.3
  • 55
    • 11844282141 scopus 로고    scopus 로고
    • For the use of chiral α,β-unsaturated amides bearing (S,S)-bis(α-methylbenzyl)amine as a building block, see:
    • For the use of chiral α,β-unsaturated amides bearing (S,S)-bis(α-methylbenzyl)amine as a building block, see:. Sato M., Gunji Y., Ikeno T., and Yamada T. Chem. Lett. 33 (2004) 1304-1305
    • (2004) Chem. Lett. , vol.33 , pp. 1304-1305
    • Sato, M.1    Gunji, Y.2    Ikeno, T.3    Yamada, T.4
  • 60
    • 0010296068 scopus 로고
    • For the use of chiral α,β-unsaturated amides bearing (S)-phenylglycine methyl ester as building block, see:
    • For the use of chiral α,β-unsaturated amides bearing (S)-phenylglycine methyl ester as building block, see:. Ronald G., and William A. Tetrahedron 44 (1988) 1523-1534
    • (1988) Tetrahedron , vol.44 , pp. 1523-1534
    • Ronald, G.1    William, A.2
  • 64
    • 4744338689 scopus 로고    scopus 로고
    • For the use of chiral α,β-unsaturated amides bearing (S)-phenylglycinol in asymmetric synthesis, see:
    • For the use of chiral α,β-unsaturated amides bearing (S)-phenylglycinol in asymmetric synthesis, see:. Tarver J.E., Terranova K.M., and Joullié M.M. Tetrahedron 60 (2004) 10277-10284
    • (2004) Tetrahedron , vol.60 , pp. 10277-10284
    • Tarver, J.E.1    Terranova, K.M.2    Joullié, M.M.3
  • 73
    • 35548981461 scopus 로고    scopus 로고
    • note
    • 2O mixture afforded the ester-amide derivative, which by Michaelis-Arbuzov reaction with trimethyl phosphite and subsequent hydrolysis using LiOH led to phosphonoacetamide 7 in 61% overall yield from l-phenylglycinol.
  • 76
    • 33847679071 scopus 로고    scopus 로고
    • For the biological evaluation of phosphonoamides, see:
    • For the biological evaluation of phosphonoamides, see:. Eldo J., Heng S., and Kantrowitz E.R. Bioorg. Med. Chem. Lett. 17 (2007) 2086-2090
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 2086-2090
    • Eldo, J.1    Heng, S.2    Kantrowitz, E.R.3
  • 82
    • 0001311213 scopus 로고
    • 3SiCl in dry THF at 0 °C, following the procedure described by:
    • 3SiCl in dry THF at 0 °C, following the procedure described by:. Nicolás E., Russell K.C., and Hruby V.J. J. Org. Chem. 58 (1993) 766-770
    • (1993) J. Org. Chem. , vol.58 , pp. 766-770
    • Nicolás, E.1    Russell, K.C.2    Hruby, V.J.3
  • 88
    • 0141747457 scopus 로고    scopus 로고
    • For the HWE reaction of phosphonoamides using DBU as a base and additives, see:
    • For the HWE reaction of phosphonoamides using DBU as a base and additives, see:. Goodman S.N., and Jacobsen E.N. Adv. Synth. Catal. 344 (2002) 953-956
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 953-956
    • Goodman, S.N.1    Jacobsen, E.N.2
  • 92
    • 35549001466 scopus 로고    scopus 로고
    • note
    • 1H NMR, a 98:02 E:Z ratio was established.
  • 93
    • 3242718533 scopus 로고    scopus 로고
    • For HWE reaction at several temperatures, see:
    • For HWE reaction at several temperatures, see:. Sano S., Takemoto Y., and Nagao Y. Arkivoc (2003) 93-101
    • (2003) Arkivoc , pp. 93-101
    • Sano, S.1    Takemoto, Y.2    Nagao, Y.3
  • 95
    • 0000744486 scopus 로고    scopus 로고
    • For the HWE reaction of phosphonoamides bearing α-amino acids, see: Also, see: Refs. 6n,q,u
    • For the HWE reaction of phosphonoamides bearing α-amino acids, see:. Blaskovich M.A., and Kahn M. J. Org. Chem. 63 (1998) 1119-1125 Also, see: Refs. 6n,q,u
    • (1998) J. Org. Chem. , vol.63 , pp. 1119-1125
    • Blaskovich, M.A.1    Kahn, M.2
  • 97
    • 35548956520 scopus 로고    scopus 로고
    • note
    • For the preparation of (R)-14a, see Ref. 13d.
  • 98
    • 35548973532 scopus 로고    scopus 로고
    • note
    • For the preparation of (R)-14b, see Ref. 13h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.