Radical cyclisation of hept-1-enitols.
7-Deoxy-7-iodohept-1-enitols react intramolecularly to give 5-carba analogues of pyranoses (pseudo sugars) by the action of tributyltin hydride, which generates a radical at C-7. The configuration at the new chiral centre depends on the relative orientation of the oxygen functions in the starting material and the pattern of substitution.
Redlich
H
H
Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, F.R.G.
Sudau
W
W
Szardenings
A K
AK
Vollerthun
R
R
D003500:Cyclization; D006536:Heptanes / Q000737:chemistry*; D006539:Heptoses / Q000737:chemistry*; D007536:Isomerism; D013402:Sugar Alcohols / Q000737:chemistry*
D006536:Heptanes; D006539:Heptoses; D013402:Sugar Alcohols