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Volumn 64, Issue 18, 1999, Pages 6554-6565

Stereoselective Michael addition of glycine anions to chiral fischer alkenylcarbene complexes. Asymmetric synthesis of β-substituted glutamic acids

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID DERIVATIVE; GLYCINE;

EID: 0032888523     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9819739     Document Type: Article
Times cited : (60)

References (89)
  • 1
    • 0028355337 scopus 로고
    • (a) For a recent review, see: Duthaler, R. O. Tetrahedron 1994, 50, 1539.
    • (1994) Tetrahedron , vol.50 , pp. 1539
    • Duthaler, R.O.1
  • 40
    • 0028300898 scopus 로고
    • and relevant references therein
    • (f) O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507 and relevant references therein. For an application to solid-phase synthesis of α,α-disubstituted amino acids and solid-phase unnatural peptide synthesis, see:
    • (1994) Tetrahedron , vol.50 , pp. 4507
    • O'Donnell, M.J.1    Wu, S.2    Huffman, J.C.3
  • 54
    • 0345134434 scopus 로고    scopus 로고
    • For a unique experiment see ref 6d
    • For a unique experiment see ref 6d.
  • 58
    • 0024354673 scopus 로고
    • For other asymmetric syntheses of 3-substituted glutamic acid derivatives through Michael addition of alkyllithiums or organocuprates to appropriately substituted chiral Michael acceptors, see: (a) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3799
    • Yanagida, M.1    Hashimoto, K.2    Ishida, M.3    Shinozaki, H.4    Shirahama, H.5
  • 66
  • 75
    • 0344703855 scopus 로고    scopus 로고
    • note
    • -1, F(000) = 1672, T = 293(2) K; final conventional R = 0.050 for 2642 "observed" reflections and wR2 = 0.161 (for all reflections) and 513 variables; GOF = 0.974; Flack's parameter χ = 0.05(4). Full details are available in the Supporting Information.
  • 77
    • 0344703854 scopus 로고    scopus 로고
    • note
    • Either anti (see refs 2a, 6c,d, 13e,f, and 15a) or syn (see refs 4c and 13a) selective Michael additions of glycine synthon anions to different α,β-unsaturated esters have been previously observed. As indicated in ref 13a these opposite results could be related with the structure of the glycine enolate reacting either as a 2-azaallylanion, which led to the anti adduct, or as an 1-oxaallylanion leading to the syn adduct when no possibility of formation of the 2-azaallylanion structure exists.
  • 87
    • 0344703853 scopus 로고    scopus 로고
    • note
    • 3N (2.5 equiv) in THF, 30 min, 25 °C, quantitative yield, and hydrogenation of compound 9f (5% Pd/ C, 30% weight) in EtOAc, 15 h, 25 °C, 65% yield.
  • 88
    • 0345565988 scopus 로고    scopus 로고
    • note
    • -3 in 6 M HCl) = +11.1.
  • 89
    • 0345134432 scopus 로고    scopus 로고
    • note
    • -3 in 6 M HCl) = +19.15.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.