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Volumn 42, Issue 43, 2003, Pages 5342-5345

Highly Diastereoselective Conjugate Addition to Alkylidene Bis(Sulfoxides): Asymmetric Synthesis of (+)-erythro-Roccellic Acid

Author keywords

Allylic compounds; Asymmetric synthesis; Michael addition; Sulfoxides; Total synthesis

Indexed keywords

ADDITION REACTIONS; CHELATION; SULFUR; SYNTHESIS (CHEMICAL);

EID: 0344012931     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352356     Document Type: Article
Times cited : (45)

References (40)
  • 2
    • 0000597854 scopus 로고
    • (Ed.: M. F. Semmelhack), Pergamon, Oxford
    • H.-G. Schmalz in Comprehensive Organic Synthesis, Vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, pp. 199-236.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 199-236
    • Schmalz, H.-G.1
  • 20
    • 0344871222 scopus 로고    scopus 로고
    • note
    • CCDC 213619-213621 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 27
    • 0344008104 scopus 로고    scopus 로고
    • note
    • The S absolute configurations of 5 and 6 were determined by correlation: (R)-5 was made independently from (R)-phenylglycinol, and LAH reduction of 6 afforded (S)-5 with no loss of optical purity and with completely opposite optical activity, see the Supporting Information.
  • 28
    • 0344439366 scopus 로고    scopus 로고
    • note
    • The absolute configuration of 7 was determined by chemical correlation, see the Supporting Information.
  • 29
    • 0002377420 scopus 로고
    • see the Supporting Information
    • The absolute configuration of 12 was determined by chemical correlation with a compound described by G. Tsuchihashi, S. Mitamura, S. Inoue, K. Ogura, Tetrahedron Lett. 1973, 14, 323, see the Supporting Information.
    • (1973) Tetrahedron Lett. , vol.14 , pp. 323
    • Tsuchihashi, G.1    Mitamura, S.2    Inoue, S.3    Ogura, K.4
  • 33
    • 0004246896 scopus 로고    scopus 로고
    • (Ed.: N. Krause), Wiley-VCH, Weinheim
    • For the mechanism of copper-mediated addition reactions, see: S. Mori, E. Nakamura in Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002.
    • (2002) Modern Organocopper Chemistry
    • Mori, S.1    Nakamura, E.2
  • 34
    • 0344008101 scopus 로고    scopus 로고
    • note
    • The R absolute configurations of 16a and 16d were determined by chemical derivatization. Pummerer reactions followed by reduction provided known enantiopure alcohols (see the Supporting Information).
  • 35
    • 0344008102 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 02/24190A1, 2002
    • G. Geisslinger, S. Grösch, PCT Int. Appl. WO 02/24190A1, 2002.
    • Geisslinger, G.1    Grösch, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.