Diastereoselectivity in the [2, 3]-sigmatropic rearrangement of substituted allylic N, N-dialkylamidosulfoxylates. X-ray molecular structure of [(1′) S*,(S) S*]-(2′ E)-4-[[ …
By the reaction with three N, N-dialkylamidosulfenyl chlorides 2 bearing representative sizes for the R groups on the nitrogen atom, several substituted secondary E or Z allylic alcohols (1a-h) have been converted into the corresponding pairs of diastereoisomeric allylic sulfinamides (3+-3′ av), whose ratios have been determined by 1H NMR spectroscopy. Five cases of entirely diastereoselective [2, 3]-sigmatropic rearrangement have been ...
