J. Crandall, D. Batal, D. Sebesta
Feb 1, 1991
Citations
0
Influential Citations
34
Citations
Journal
Journal of Organic Chemistry
Abstract
A number of simple allenes have been converted cleanly to the corresponding 1,4-dioxaspiro [2.2] pentanes in good yields by oxidation with dimethyldioxirane. Mono- and trisubstituted allenes give the anti diastereomers with good stereoselectivity, whereas 1,3-disubstituted allenes show only a slight preference for the anti,anti isomers, unless steric effects are extreme. Stereochemical assignments are based on steric considerations and a consistent set of NMR characteristics that permit structural attributions