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-[[3′-(4″-bromophenyl)-1′-methyl-2′-propenyl]sulfinyl]-morpholine
作者:Jean-Bernard Baudin、Itka Bkouche-Waksman、Georges Hareau、Sylvestre A. Julia、Robert Lorne、Claudine Pascard
DOI:10.1016/s0040-4020(01)82318-8
日期:1991.8
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′a-v), whose ratios have been determined by 1H NMR spectroscopy. Five cases of entirely diastereoselective [2,3]-sigmatropic
通过与三个N,N-二烷基酰胺基亚磺酰氯2(在氮原子上具有代表性的R基团)反应,一些取代的仲E或Z烯丙基醇(1a-h)已转化为相应的非对映异构烯丙基亚磺酰胺(3 + -3'av),其比例已通过1 H NMR光谱测定。已经观察到五例完全非对映选择性[2,3]-σ重排的情况。