Search for ideal sulfinyl dienophile and dipolarophile

By analysis, the advantages and drawbacks of the differently substituted vinyl sulfoxides so far reported, (Z)-3-p-tolylsulfinyl acrylonitriles are proposed as the best sulfinyl dienophiles. The stereoselective synthesis of these compounds was optimized by hydrocyanation of sulfinyl alkynes with Et2AlCN. Their behavior as chiral dienophiles and dipolarophiles is responsible for the high stereocontrol of Diels–Alder and 1,3-dipolar reactions, respectively. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:453–462, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10066