The catalytic asymmetric aminohydroxylation (AA) of 5-substituted-pent-2-enoates 8 and 17 was investigated as a route to 2,3,6-trideoxy-3-aminohexoses. The AA of ester 8, which bears a dimethyl acetal at C-5, favoured formation of the a-amino regioisomer 11 with optimum regioselectivity being observ
A dihydroisoxazole-based route to 2,3,6-trideoxy-3-aminohexose derivatives
β Scribed by Peter A. Wade; J.Appa Rao; James F. Bereznak; C.-K. Yuan
- Book ID
- 104244912
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 256 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Acosamine and ristosamine derivatives were prepared via stereoselective reductive cleavage reactions of a benzylidenated dihydroisoxazolyl diol; the diol was prepared from 3-nitro-4,5dihydroisoxazole via sequential propynylation, Lindlar reduction, and catalytic hydroxylation.
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## Abstract An efficient route to 2β²,3β²βdihydroβ2β²βthioxospiro[indoleβ3,6β²β[1,3]thiazin]β2(1__H__)βone derivatives is described. It involves the reaction of isatine, 1βphenylβ2β(1,1,1βtriphenylβ__Ξ»__^5^βphosphanylidene)ethanβ1βone, and different amines in the presence of CS~2~ in dry MeOH at reflux