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Asymmetric synthesis of pentono- and 6-deoxyhexono-δ-lactams via hetero-Diels-Alder reactions with nitroso dienophile

✍ Scribed by Albert Defoin; Hervé Sarazin; Thierry Sifferlen; Christiane Strehler; Jacques Streith


Publisher
John Wiley and Sons
Year
1998
Tongue
German
Weight
803 KB
Volume
81
Category
Article
ISSN
0018-019X

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Synthesis of 1,6-Dideoxynojirimycin, 1,6
✍ Albert Defoin; Hervé Sarazin; Jacques Streith 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 German ⚖ 503 KB

## Abstract Asymmetric __Diels‐Alder__ reaction of sorbaldehyde __O__‐methyloxime 1d with chiral chloronitroso derivative 2 of D‐mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%; __Scheme 1__). Catalytic hydrogenolysis of 6a gave