DERIVATIVES OF 1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE FOR DIELS-ALDER REACTIONS

The preparation and Diels-Alder cycloadditions of the following highly functionalized drenes are described: (1) (E)-1-methoxy-2-methyl-3-trimethylsilyloxy-1,3-butadiene (5), (2) (E.Z)-1 -methoxy-3-trimethylsiiyloxy-4-methyl-1,3-butadiene (6), (3) (E,Z)-l-methoxy-2,4-dimethyl-3-trimethylsilyloxy-l,3-butadiene (7), (4) (E,Z)-l-methoxy-3-trimethylsilyloxy-1,3-butadiene (25), and (5) 1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene (46). The use of these dienes in Diels-Alder reactions enables rapid access to diversely functionalized aromatics, cyclohexenones, cyclohexadienones, and 3-methoxycyclo-hexenones. © 1979, American Chemical Society. All rights reserved.