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Volumn , Issue 20, 2006, Pages 3389-3396

Enantioselective synthesis of 1,4-dihydrobenzoxathiins via sulfoxide-directed borane reduction

Author keywords

Asymmetric synthesis; Dihydrobenzoxathiin; Reduction; Sulfoxide

Indexed keywords

REACTION KINETICS; REDUCTION; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 33750589329     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950243     Document Type: Article
Times cited : (8)

References (37)
  • 10
    • 0008840910 scopus 로고
    • and references cited therein
    • The reduction of sulfoxides to sulfides with borane reagents has been reported, see: Cha, J. S.; Kim, J. E.; Kim, J. D. Tetrahedron Lett. 1985, 26, 6453; and references cited therein.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 6453
    • Cha, J.S.1    Kim, J.E.2    Kim, J.D.3
  • 14
    • 0002269209 scopus 로고
    • (a) This mechanism differs from the hydroboration-type reaction observed on enamino sulfoxides, see: Ogura, K.; Tomori, H.; Fujita, M. Chem. Lett. 1991, 1407.
    • (1991) Chem. Lett. , pp. 1407
    • Ogura, K.1    Tomori, H.2    Fujita, M.3
  • 15
    • 33750577531 scopus 로고    scopus 로고
    • note
    • (b) Additional details and discussion of the proposed mechanism can be found in reference 5.
  • 16
    • 0000391481 scopus 로고
    • For examples of measured kinetic isotope effects for borane reductions, see: (a) Hawthorne, F. M.; Lewis, E. S. J. Am. Chem. Soc. 1958, 80, 4296.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 4296
    • Hawthorne, F.M.1    Lewis, E.S.2
  • 30
    • 33750595712 scopus 로고    scopus 로고
    • note
    • 2O (0.15 mol%) as the catalyst and cumene hydroperoxide (CHP, 1.2 equiv) as the oxidant. See ref 5.
  • 31
    • 33750576133 scopus 로고    scopus 로고
    • note
    • Compounds 5f and 6f were prepared previously, see reference 5 for experimental details.
  • 32
    • 33750595102 scopus 로고    scopus 로고
    • note
    • 2. The substrate was added to the catalyst solution followed by cumene hydroperoxide (CHP).
  • 33
    • 33750597233 scopus 로고    scopus 로고
    • note
    • int = 0.0421), 18173 reflections collected; refinement method, full-matrix least squares refinement on F2; Goodness-of-fit on F2 = 1.024; Final R indices [I > 2σ(I)] R1 = 0.0412, wR2 = 0.0958.
  • 34
    • 33750596053 scopus 로고    scopus 로고
    • note
    • A tentative assignment of the S-configuration for 6a-e and 7a-d can be made based on the mechanism and analogy to 7e. This is consistent with the facial selectivity previously reported by us (see ref. 5).
  • 35
    • 33750597087 scopus 로고    scopus 로고
    • Japanese Patent JP11029515, 1999
    • Suetsugu, M.; Fujiwara, R. Japanese Patent JP11029515, 1999; Chem. Abstr. 1999, 130, 200767.
    • (1999) Chem. Abstr. , vol.130 , pp. 200767
    • Suetsugu, M.1    Fujiwara, R.2
  • 37
    • 33750598996 scopus 로고    scopus 로고
    • note
    • Initially, this sequence was done on commercially available 3-benzyloxy-4-methoxy benzaldehyde; however, the dehydrative cyclization failed to give the desired product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.