Sulfoxide-directed intramolecular [4 + 2] cycloadditions between 2-sulfinyl butadienes and unactivated alkynes.

Sulfinyl dienynes undergo thermal and catalyzed IMDA cycloadditions, often at room temperature, to produce cyclohexa-1,4-dienes with good yields and high selectivities. Additionally, the products preserve a synthetically useful vinyl sulfoxide functionality. The selective manipulation of the double bonds in the cycloadducts has also been examined in this work.

Sulfoxide-directed thermal intramolecular [4 + 2] cycloadditions between 2-sulfinyl butadienes and unactivated alkynes.

2-Sulfinyl butadienes tethered to unactivated alkynes undergo a facile thermal intramolecular Diels-Alder cycloaddition, often at room temperature, to produce cyclohexa-1,4-dienes with good selectivities, in high yields, and preserving the valuable vinyl sulfoxide functionality.