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Regioselective asymmetric aminohydroxylation of precursors to 2,3,6-trideoxy-3-aminohexoses

โœ Scribed by Roger M Davey; Margaret A Brimble; Malcolm D McLeod *

Book ID
104210484
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
248 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 observed using (DHQ) 2 AQN as the chiral ligand and the chloramine salt of ethyl carbamate as the nitrogen source. Ester 17, which has a 4-methoxyphenoxy group at C-5, undergoes highly regioselective AA aording the b-amino regioisomer 19 in excellent enantiomeric excess, thereby establishing that introduction of this aromatic group leads to a superior substrate for AA.

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