Construction of 4‑Vinyl-1,2-oxaphospholane 2‑Oxides from Vinyloxiranes and Phosphoryl Diazomethanes

Various 4-vinyl-1,2-oxaphospholane 2-oxides are prepared
in good
to excellent yields from vinyloxiranes and in situ-generated phosphenes
from phosphoryl diazomethanes via the phosphene-induced ring expansion
of oxiranes. The reaction is a novel and expeditious strategy for
the synthesis of 1,2-oxaphospholane 2-oxide derivatives, featuring
ring expansion of readily available starting materials, high atom
economy, no catalyst, a fast reaction rate, broad functional group
tolerance, high yields, and separable diastereomers.