INTERMOLECULAR AND INTRAMOLECULAR [4+2] CYCLOADDITIONS OF NITROALKENES WITH OLEFINS - 2-NITROSTYRENES
INTERMOLECULAR AND INTRAMOLECULAR [4+2] CYCLOADDITIONS OF NITROALKENES WITH OLEFINS - 2-NITROSTYRENES
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DOI：
10.1021/jo00044a029
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发表时间：
1992-08-28
影响因子：
3.6
通讯作者：
MOON, YC
中科院分区：
文献类型：
--
作者：
DENMARK, SE;KESLER, BS;MOON, YC
Aromatic nitroalkenes 9-12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitronates 25-30 with exclusive anti selectivity. Hammett studies helped to further delineate the role of the Lewis acid. Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions. The major products were the syn diastereomers which arise from an endo-folded transition structure. Finally, intramolecular cycloaddition of 36-39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.
