Protecting group and solvent control of stereo- and chemoselectivity in glucal 3-carbamate amidoglycosylation
Gupta, R; Sogi, KM; Bernard, SE; Decatur, JD; Rojas, CM
| HERO ID | 4947926 |
|---|---|
| In Press | No |
| Year | 2009 |
| Title | Protecting group and solvent control of stereo- and chemoselectivity in glucal 3-carbamate amidoglycosylation |
| Authors | Gupta, R; Sogi, KM; Bernard, SE; Decatur, JD; Rojas, CM |
| Journal | Organic Letters |
| Volume | 11 |
| Issue | 7 |
| Page Numbers | 1527-1530 |
| Abstract | In the Rh(2)(OAc)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 4O and 6O protecting groups. Acyclic protection permits high alpha-anomer selectivity with further improvement in less polar solvents, while electron-withdrawing protecting groups limit C3-oxidized byproducts. Stereocontrol and bifurcation between alkene insertion and C3-H oxidation reflect an interplay of conformational, stereoelectronic, and inductive factors. |
| Doi | 10.1021/ol900126q |
| Pmid | 19254041 |
| Wosid | WOS:000264622600017 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-64349108311&doi=10.1021%2fol900126q&partnerID=40&md5=e619c135d34a61262c6afe3ecbebce43 |
| Is Public | Yes |
| Language Text | English |
| Keyword | carbamic acid derivative; drug derivative; gluconate calcium; hexosamine; mannosamine; mannose; oxazolidinone derivative; article; catalysis; chemical structure; chemistry; combinatorial chemistry; glycosylation; stereoisomerism; synthesis; Calcium Gluconate; Carbamates; Catalysis; Combinatorial Chemistry Techniques; Glycosylation; Hexosamines; Mannose; Molecular Structure; Oxazolidinones; Stereoisomerism |