New uses for the Burgess reagent in chemical synthesis: methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides.
Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic tasks when applied to appropriate substrates, such as the formation of sulfamidates from 1,2-diols or epoxyalcohols, alpha- and beta-glycosylamines from carbohydrates, and cyclic sulfamides from 1,2-aminoalcohols. Beyond delineating the power of these new reaction manifolds, we also describe the construction of a group of alternative Burgess-type reagents that extends the scope of these new reactions even further.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu
Snyder
Scott A
SA
Longbottom
Deborah A
DA
Nalbandian
Annie Z
AZ
Huang
Xianhai
X
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D006031:Glycosylation; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D013696:Temperature
D000577:Amides; D000588:Amines; D000605:Amino Alcohols; D002219:Carbamates; D002241:Carbohydrates; D004852:Epoxy Compounds; D013455:Sulfur