Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine.
[reaction: see text] The carbamate-protected glycals of naturally occurring 3,4-cis-3-amino-2,3,6-trideoxyhexoses (l-daunosamine, d-saccharosamine, and l-ristosamine) were prepared from noncarbohydrate starting materials. The short, high-yield syntheses are based on the chemoselective insertion of a rhodium nitrene in an allylic C-H bond rather than in a C-H bond that is alpha to an oxygen substituent.
Parker
Kathlyn A
KA
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA. kparker@notes.cc sunysb.edu
Chang
Wonsuk
W
D002384:Catalysis; D006595:Hexosamines / Q000138:chemical synthesis*; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D006595:Hexosamines; D017672:Nitrogen Compounds; C007217:daunosamine; C001946:vancosamine; C010783:ristosamine; D012238:Rhodium