메뉴 건너뛰기




Volumn 44, Issue 10, 2005, Pages 1543-1545

The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids

Author keywords

Aldol reaction; Amino acids; Asymmetric catalysis; Lewis acids; Magnesium

Indexed keywords

ALDEHYDES; ANTIBIOTICS; CATALYST ACTIVITY; MAGNESIUM PRINTING PLATES; SYNTHESIS (CHEMICAL);

EID: 16244397120     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462125     Document Type: Article
Times cited : (95)

References (36)
  • 1
    • 16244406498 scopus 로고
    • (Ed.: R. Nagarajan), Marcel Dekker, New York
    • Glycopeptide Antiobiotics, (Ed.: R. Nagarajan), Marcel Dekker, New York, 1994.
    • (1994) Glycopeptide Antiobiotics
  • 6
    • 0001768006 scopus 로고    scopus 로고
    • For a discussion of the different approaches used to prepare the β-hydroxy-tyrosine units found in glycopeptide antibiotics, see: K. C. Nicolaou, C. N. C. Boddy, S. Eräse, N. Winssinger, Angew. Chem. 1999, 111, 2230; Angew. Chem. Int. Ed. 1999, 38, 2096.
    • (1999) Angew. Chem. , vol.111 , pp. 2230
    • Nicolaou, K.C.1    Boddy, C.N.C.2    Eräse, S.3    Winssinger, N.4
  • 7
    • 0033516914 scopus 로고    scopus 로고
    • For a discussion of the different approaches used to prepare the β-hydroxy-tyrosine units found in glycopeptide antibiotics, see: K. C. Nicolaou, C. N. C. Boddy, S. Eräse, N. Winssinger, Angew. Chem. 1999, 111, 2230; Angew. Chem. Int. Ed. 1999, 38, 2096.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2096
  • 9
    • 2942652053 scopus 로고    scopus 로고
    • For recent examples, see: a) K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882, for ketone reductions;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 882
  • 22
    • 0035907043 scopus 로고    scopus 로고
    • b) D. A. Evans, J. M. Janey, N. Magomedov, J. S. Tedrow, Angew. Chem. 2001, 113, 1936; Angew. Chem. Int. Ed. 2001, 40, 1884;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1884
  • 26
    • 0037011290 scopus 로고    scopus 로고
    • e) T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 4724; Angew. Chem. Int. Ed. 2002, 41, 4542.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4542
  • 28
    • 16244397996 scopus 로고    scopus 로고
    • note
    • Oxazolidinone 3 was prepared from the corresponding azide, according to the procedure reported for a chiral derivative in Reference [12a]. See Supporting Information for details.
  • 29
    • 0022490196 scopus 로고
    • For examples of the use of a chiral version of 3 in diastereoselective aldol additions, see: a) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757;
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6757
    • Evans, D.A.1    Weber, A.E.2
  • 34
    • 16244417718 scopus 로고    scopus 로고
    • note
    • The addition of 20 mol % water to the reaction resulted in a significant reduction in the enantioselectivity of the process (50-60% ee depending on the exact reaction).
  • 35
    • 16244376743 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the benzaldehyde adduct (Table 2, entry 1) was established by X-ray crystallography; the remaining adducts are assigned by analogy.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.