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Volumn 71, Issue 4, 2006, Pages 1442-1448

Synthesis of highly substituted enantiopure piperazines and ketopiperazines from vicinal N-sulfinyl diamines

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROACETYL CHLORIDE; ENANTIOPURE PIPERAZINES; KETOPIPERAZINES; N-SULFINYL DIAMINES;

EID: 33644535452     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052077h     Document Type: Article
Times cited : (39)

References (65)
  • 15
    • 0035844405 scopus 로고    scopus 로고
    • and references therein
    • For other piperazines with significant biological actitvity, see: (b) Bedürftig, S.; Weigl, M.; Wünsch, B. Tetrahedron: Asymmetry 2001, 12, 1293-1302 and references therein.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1293-1302
    • Bedürftig, S.1    Weigl, M.2    Wünsch, B.3
  • 21
    • 0035955155 scopus 로고    scopus 로고
    • For other biologically active ketopiperazines, see: (a) Govek, S. P.; Overman, L. E. J. Am. Chem. Soc. 2001, 123, 9468-9469.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9468-9469
    • Govek, S.P.1    Overman, L.E.2
  • 51
    • 33644529577 scopus 로고    scopus 로고
    • note
    • We have speculated about secondary processes caused by the acidity of the amide (CONH) and the carbon α-to the ester; however, the precise origin of the failure of these cyclizations remains unclear.
  • 58
    • 0037145019 scopus 로고    scopus 로고
    • For leading references, see: (a) Kulesza, A.; Mieczkowski, A.; Jurczak, J. Tetrahedron: Asymmetry 2002, 13, 2061-2069.
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 2061-2069
  • 64
    • 33644552936 scopus 로고    scopus 로고
    • note
    • 2O and CHiPr protons were observed (see Supporting Information).
  • 65
    • 0037463738 scopus 로고    scopus 로고
    • 2OP, and Bn) for N-sulfinyl ketopiperazines 8 and imino ketopiperazines 9 that was confirmed by DNOE experiments (see Experimental Procedures). For a related example, see: (a) Knapp, S.; Morriello, G. J.; Doss, G. A. Tetrahedron Lett. 2003, 44, 2645-2647.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2645-2647
    • Knapp, S.1    Morriello, G.J.2    Doss, G.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.