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Volumn 48, Issue 17, 2009, Pages 3165-3169

Stereodivergent de novo synthesis of branched amino sugars by lewis acid promoted rearrangement of 1,2-oxazines

Author keywords

[No Author keywords available]

Indexed keywords

AMINO SUGAR; BICYCLIC PRODUCTS; DE NOVO SYNTHESIS; LEWIS ACID; LEWIS ACIDIC; STEREOCONTROL;

EID: 70349784899     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805724     Document Type: Article
Times cited : (34)

References (58)
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    • For C-branched sugars: a) Y. Chapleur, F. Chrétien in Preparative Carbohydrate Chemistry (Ed.: S. Hanessian), Marcel Dekker, New York, 1997, pp. 204-262;
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    • (a) A. Al-Harrasi, H.-U. Reissig, Angew. Chem. 2005, 117, 6383-6387; Angew. Chem. Int. Ed. 2005, 44, 6227-6231;
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    • first application: J. Dernedde, S. Enders, H.-U. Reissig, M. Roskamp, S. Schlecht, S. Yekta, Chem. Commun. 2009, 932-934.
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    • The Lewis acid probably coordinates to the external oxygen atom of the dioxolane moiety of syn/anti-3 leading to a ring opening, and then an attack of the resulting carbenium ion onto the enol ether double bond. Finally fragmentation of the TMSE group generates the central carbonyl group of bicycles 6-8 (see reference [9]).
    • The Lewis acid probably coordinates to the external oxygen atom of the dioxolane moiety of syn/anti-3 leading to a ring opening, and then an attack of the resulting carbenium ion onto the enol ether double bond. Finally fragmentation of the TMSE group generates the central carbonyl group of bicycles 6-8 (see reference [9]).
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    • First experiments reveal that phenylseleno-substituted 1,2-oxazines may also be used: F. Pfrengle, H.-U. Reissig, unpublished results.
    • First experiments reveal that phenylseleno-substituted 1,2-oxazines may also be used: F. Pfrengle, H.-U. Reissig, unpublished results.
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    • The TBSOTf-induced rearrangement was unsuccessful in case of anti-3.
    • The TBSOTf-induced rearrangement was unsuccessful in case of anti-3.
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    • The synthesis of non-glycosidic compounds is also possible. This possibility could serve for the construction of linear or branched oligosaccharide mimetics (see F. Sicherl, V. Wittmann, Angew. Chem. 2005, 117, 2133-2136; Angew. Chem. Int. Ed. 2005, 44, 2133-2136) or achieve the geometrically defined presentation of ligands (see U. Hünger, J. Ohnsmann, H. Kunz, Angew. Chem. 2004, 116, 1125-1128; Angew. Chem. Int. Ed. 2004, 43, 1104-1107).
    • The synthesis of non-glycosidic compounds is also possible. This possibility could serve for the construction of linear or branched oligosaccharide mimetics (see F. Sicherl, V. Wittmann, Angew. Chem. 2005, 117, 2133-2136; Angew. Chem. Int. Ed. 2005, 44, 2133-2136) or achieve the geometrically defined presentation of ligands (see U. Hünger, J. Ohnsmann, H. Kunz, Angew. Chem. 2004, 116, 1125-1128; Angew. Chem. Int. Ed. 2004, 43, 1104-1107).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.