ALPHA-OXOSULFINES .1. REACTIVITY OF ALPHA-OXOSULFINES OBTAINED FROM RETRO-DIELS-ALDER REACTION OF 1,4-OXATHIIN-S-OXIDES

Oxidation of 1,4-oxathiin derivatives 10-16 affords the corresponding sulfoxides 17-26 in high yield and good stereoselectivity. The oxathii n-S-oxides undergo a Retro Diels-Alder (RDA) reaction to form alpha-ox osulfines under very mild conditions. These reactive intermediates can be successfully trapped as dienophiles or as electron poor dienes in Inverse Electron Demand Diels-Alder reaction (IEDDA). The relationship between the structure of the starting sulfoxide, the geometry of the intermediate sulfine and the stereochemistry of the final cycloadduct have been tentatively correlated. Copyright (C) 1996 Published by Else vier Science Ltd