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Synthesis of optically active amino sugar derivatives using catalytic enantioselective hetero-Diels–Alder reactions

✍ Scribed by Zhuang, Wei; Thorhauge, Jacob; Jørgensen, Karl Anker


Book ID
120465387
Publisher
Royal Society of Chemistry
Year
2000
Tongue
English
Weight
65 KB
Volume
6
Category
Article
ISSN
1359-7345

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The thermally induced hetero-Diels-Alder reaction of vinyl ethers 2a-d and Nacylenaminones 3a-h leads to the diastereomeric adducts 4a-h and 5a-h in 75 -98 % yield providing cis-compounds 4a-h as the main products. Isomerisation of 4a-f with Lewis acids gives theXermodynamically more stable 5a-f. Tr