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Volumn , Issue 19, 2003, Pages 3818-3826

Enantioselective Strecker reactions between aldimines and trimethylsilyl cyanide promoted by chiral N,N′-dioxides

Author keywords

Amino acids; Asymmetric synthesis; Enantioselectivity; Lewis bases; Nitrogen oxides

Indexed keywords

3,3' DIMETHYL 2,2' BIQUINOLINE N,N' DIOXIDE; AMINO ACID; BASE; CYANIDE; IMINE; LEWIS BASE; NITRILE; NITROGEN OXIDE; OXIDE; QUINOLINE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141891472     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300319     Document Type: Article
Times cited : (107)

References (86)
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    • note
    • For the resolution of rac-1, see: Supporting Information of ref.[12b]
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    • CCDC-217323 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
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    • note
    • With 1 equiv. of HCN in the absence of chiral N,N′-dioxides, the reaction gave traces of product after 24 h; and with 2 equiv. of HCN under the same conditions, the product was obtained in 39% yield after 30 h.
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    • note
    • We found that TMSCN could act as another effective cyanide source in the presence of chiral N,N′-dioxide 2 and that the reaction with use of TMSCN instead of HCN at 0 °C afforded the product in better yield with similar enantioselectivity.
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    • note
    • For preparation of imines, see: Supporting Information of ref.[6c]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.