Lewis Acid promoted tandem intermolecular Diels-Alder/intramolecular allylation reactions of silyl-substituted 1,3-butadienes leading to multisubstituted 7-norbornenones and related polycyclic compounds.
7-Norbornenones of exo,exo-disubstituted patterns were formed highly selectively in good yields from Lewis acid-promoted tandem intermolecular Diels-Alder/intramolecular allylation reactions. The intermolecular Diels-Alder reaction between 1,4-bis(trimethylsilyl)-1,3-butadienes or 1-trimethylsilyl-1,3-butadienes with maleic anhydride in the presence of newly sublimed AlCl3 afforded their corresponding cycloaddition adducts, which underwent AlCl3-mediated intramolecular allylation of the carbonyl group by the in situ generated allylsilane moiety affording 7-norbornenones of exo,exo-disubstituted patterns.
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Dongzhen
D
Li
Guangzhen
G
Liu
Qiaoshu
Q
Hu
Chao
C
Wang
Zhenfeng
Z
Xi
D001896:Boron Compounds / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D008958:Models, Molecular; D011083:Polycyclic Compounds / Q000737:chemistry*; D014961:X-Ray Diffraction
D001896:Boron Compounds; D002070:Butadienes; D011083:Polycyclic Compounds