INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFUR-SUBSTITUTED DIENES VIA 3-SULFOLENES

Sulfur-substituted dienes containing an unsaturated alkyl chain were readily prepared from 3-sulfolenes. The intramolecular Diels-Alder (IMDA) reaction of these derivatives was studied for the first time. A sulfonyl group on the diene was found to facilitate the IMDA reaction. Hexahydroindenes were produced in good yield and with high stereoselectivity. Octahydronaphthalenes were also obtained, but the stereoselectivity was low and the IMDA reaction was more sensitive to steric hindrance. © 1990, American Chemical Society. All rights reserved.