Iodoacetoxylation of Glycals Using Cerium(IV) Ammonium Nitrate, Sodium Iodide, and Acetic Acid:  Stereoselective Synthesis of 2-Deoxy-2-iodo-α-mannopyranosyl Acetates

The reactions of glycals with ceric(IV) ammonium nitrate and sodium iodide in the presence of acetic acid provides 2-deoxy-2-iodo-α-mannopyranosyl acetates with good stereoselectivity. In the majority of the cases examined, the selectivity was considerably better than that from reactions using N-iod...

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Bibliographic Details
Published in:Organic letters 1999-09, Vol.1 (6), p.895-897
Main Authors: Roush, William R, Narayan, Sridhar, Bennett, Chad E, Briner, Karin
Format: Article
Language:English
Subjects:
Acetates - chemical synthesis
Acetates - chemistry
Cerium - chemistry
Glucose - chemistry
Mannose - chemistry
Sodium Iodide - chemistry
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Summary:The reactions of glycals with ceric(IV) ammonium nitrate and sodium iodide in the presence of acetic acid provides 2-deoxy-2-iodo-α-mannopyranosyl acetates with good stereoselectivity. In the majority of the cases examined, the selectivity was considerably better than that from reactions using N-iodosuccinimide and HOAc.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990815g