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Volumn 60, Issue 25, 2004, Pages 5383-5392

About the stereoselectivity control in reactions of chiral ortho-sulfinyl benzyl carbanions with aldehydes

Author keywords

1 Alkyl 2 phenyl 1 propanol; 1 Aryl 2 phenyl 1 propanol; Benzylic stereocenter; Chiral benzyllithium; Remote stereocontrol; Sulfoxide

Indexed keywords

ALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; BENZYL DERIVATIVE; CARBON; LITHIUM DERIVATIVE; PROPRANOLOL DERIVATIVE;

EID: 2542482623     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.051     Document Type: Article
Times cited : (31)

References (25)
  • 13
    • 2542422192 scopus 로고    scopus 로고
    • note
    • 1H NMR (ratio anti-syn, 69:31). Nevertheless, their complete configurational assignment was not established because only the first and the last compounds could be separated
  • 15
    • 2542451316 scopus 로고    scopus 로고
    • 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]
    • Crystallographic data (excluding structure factors) for the structures 3k and 4k have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 221162 and 221163. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]
  • 16
    • 2542493426 scopus 로고    scopus 로고
    • The fact that the preferred conformation of one of these epimers displays the high sterically demandant 2,6-dimethylphenyl ring in gauche arrangement with respect to the sulfinylated ring suggests some kind of π-stacking interaction between the aromatic rings exhibiting complementary electronic density (donor-acceptor interaction)
    • The fact that the preferred conformation of one of these epimers displays the high sterically demandant 2, 6-dimethylphenyl ring in gauche arrangement with respect to the sulfinylated ring suggests some kind of π-stacking interaction between the aromatic rings exhibiting complementary electronic density (donor-acceptor interaction)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.