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Volumn 8, Issue 3, 1997, Pages 409-416

(S,S)-1,1-bis-ethoxycarbonyl-2,2-bis-p-tolylsulfinyl ethene: A highly stereoselective but unexpectedly unreactive dienophile in asymmetric Diels-Alder reactions

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOPENTADIENE DERIVATIVE; SULFOXIDE;

EID: 0031054769     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00526-5     Document Type: Article
Times cited : (21)

References (43)
  • 3
    • 0001018322 scopus 로고
    • Sheffold, R., Ed.; Springer-Verlag: Berlin, Heidelberg
    • c) Helmchen, G.; Karge, R.; Weetman, J. In Modern Synthetic Methods; Sheffold, R., Ed.; Springer-Verlag: Berlin, Heidelberg, 1986; Vol. 4, p 262.
    • (1986) Modern Synthetic Methods , vol.4 , pp. 262
    • Helmchen, G.1    Karge, R.2    Weetman, J.3
  • 35
    • 0342888347 scopus 로고    scopus 로고
    • 3N, probably due to the tendency of the sulfinyl groups to suffer Pummerer reactions
    • 3N, probably due to the tendency of the sulfinyl groups to suffer Pummerer reactions.
  • 37
    • 0342888344 scopus 로고    scopus 로고
    • note
    • We failed in all the trials to obtain crystals from 9a and 9d, suitable for X-ray diffraction studies. We had the same problem with sulfone 10 (obtained by MCPBA oxidation of 9a) and alcohol 11, (resulting in the stereoselective hydroboration of 9d) which were prepared with this aim.
  • 38
    • 0343323307 scopus 로고    scopus 로고
    • note
    • We must also consider that the stereoelectronic interactions between the geminal ester groups in rotamer A, should produce distorsions in the coplanarity decreassing its relative stability.
  • 39
    • 0343323308 scopus 로고    scopus 로고
    • note
    • The increase in the stereoselectivity observed with acyclic dienes can be explained from Figure 2. Thus, the absence of the methylene bridge will mainly stabilize the approach 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.