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Volumn 21, Issue 9-10, 2010, Pages 1311-1314

Synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2, 2′-disulfonic acids

Author keywords

BINSA; Chiral binaphthyl compound; Disulfonic acids; Electrophilic substitutions; Ortholithiation

Indexed keywords

3,3' 1,1' BINAPHTHYL 2,2' DISULFONIC ACID; 3,3' BIS(TRIMETHYLSILYL) 3,3' 1,1' BINAPHTHYL 2,2' DISULFONIC ACID; 3,3' DIBORYL 3,3' 1,1' BINAPHTHYL 2,2' DISULFONIC ACID; 3,3' DIHALO,3,3' 1,1' BINAPHTHYL 2,2' DISULFONIC ACID; BROMINE; ELECTROPHILE; IODINE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77956674904     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.014     Document Type: Article
Times cited : (21)

References (39)
  • 30
    • 0027527450 scopus 로고
    • Esterification of benzenesulfonic acid with trimethyl orthoacetate or triethyl orthoacetate. J.I. Trujillo, and A.S. Gopalan Tetrahedron Lett. 34 1993 7355
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7355
    • Trujillo, J.I.1    Gopalan, A.S.2
  • 32
    • 77956693920 scopus 로고    scopus 로고
    • note
    • Almost the same result was observed when s-BuLi was used in place of n-BuLi.
  • 33
    • 77956671960 scopus 로고    scopus 로고
    • note
    • 2 = 0.0731. GOF = 1.053. Complete crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 759444. Copies of this information may be obtained free of charge from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, UK. (fax: +44-1223-336033, e-mail: deposit@ccdc.cam.ac.uk or via: www.ccdc.cam.ac.uk ).
  • 38
    • 77956705151 scopus 로고    scopus 로고
    • note
    • 2-substituted O-thiocarbamoyl compound 19 under microwave conditions (200 °C for 25 min or 250 °C for 45 min) provided (S)-thiocarbamoyl compound 20 in 10-25% yields (Eq. 13). Significant amount of thiophene by-product 21 and a black material were obtained, although 19 was completely converted. Moreover, subsequent reduction and oxidation steps also showed unfavorable results (Eq. 14). Therefore, in sharp contrast to unsubstituted BINSA 1, the presence of substitutions at the 3,3′-positions might prevent the chemoselective Newman-Kwart rearrangement and subsequent reactions.
  • 39
    • 77956686314 scopus 로고    scopus 로고
    • note
    • 1H NMR and MS analysis were available.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.