Efficient and stereodivergent synthesis of deoxyimino sugars

Both cis- and trans-2-substituted-1,2,3,6-tetrahydro-pyridin-3-ols have been prepared via an aldol condensation–ring-closing metathesis sequence. A stereodivergent synthesis of optionally functionalized deoxyimino sugars was achieved via asymmetric dihydroxylation or epoxidation/nucleophilic substit...

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Veröffentlicht in:	Carbohydrate research 2005-11, Vol.340 (16), p.2457-2468
Hauptverfasser:	Hong, Bor-Cherng, Chen, Zhong-Yi, Nagarajan, Arumugam, Kottani, Rudresha, Chavan, Vishal, Chen, Wei-Hung, Jiang, Yea-Fen, Zhang, Shuo-Cang, Liao, Ju-Hsiou, Sarshar, Sepehr
Format:	Artikel
Sprache:	eng
Schlagworte:	Asymmetric dihydroxylation Crystallography, X-Ray Deoxy Sugars - chemical synthesis Deoxy Sugars - chemistry Imino sugar Imino Sugars - chemical synthesis Imino Sugars - chemistry Metathesis Models, Molecular Molecular Structure Stereodivergent Stereoisomerism
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Beschreibung
Zusammenfassung:	Both cis- and trans-2-substituted-1,2,3,6-tetrahydro-pyridin-3-ols have been prepared via an aldol condensation–ring-closing metathesis sequence. A stereodivergent synthesis of optionally functionalized deoxyimino sugars was achieved via asymmetric dihydroxylation or epoxidation/nucleophilic substitution of these tetrahydropyridines.
ISSN:	0008-6215 1873-426X
DOI:	10.1016/j.carres.2005.08.014