Lewis acid-mediated generation of bicyclo[5.3.0]decanes and bicyclo[4.3.0]nonanes.
Lewis acid-mediated generation of bicyclo[5.3.0]decanes and bicyclo[4.3.0]nonanes.
复制标题
路易斯酸介导生成双环[5.3.0]癸烷和双环[4.3.0]壬烷。
DOI：
10.1021/ol051498i
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发表时间：
2005
期刊：
影响因子：
5.2
通讯作者：
Snapper,MarcL
中科院分区：
文献类型：
--
作者：
Deak,HollyL;Williams,MichaelJ;Snapper,MarcL
由环丁二烯与烯烃的分子内环加成产生的含环丁烷的加合物的断裂提供了快速进入双环[5.3.0]癸烷和双环[4.3.0]壬烷环系统。而早期的研究功能的热方法，以实现所需的重排，一个温和的，刘易斯酸介导的碎片已被确定为基板与适当的功能相邻的应变环系统。底物范围和立体化学结果的酸介导的碎片是互补的热环膨胀，特别是在双环[5.3.0]癸烷的情况下。
Fragmentation of the cyclobutane-containing adducts generated from intramolecular cycloadditions of cyclobutadiene with olefins provides rapid entry into bicyclo[5.3.0]decane and bicyclo[4.3.0]nonane ring systems. Whereas earlier studies featured thermal methods to achieve the desired rearrangements, a mild, Lewis acid-mediated fragmentation has been identified for substrates with appropriate functionality adjacent to the strained ring system. The substrate scope and stereochemical outcome of the acid-mediated fragmentation are complementary to the thermal ring expansions, particularly in the case of the bicyclo[5.3.0]decanes.