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Additive Tuned Selective Synthesis of Bicyclo[3.3.0]octan-1-ols and Bicyclo[3.1.0]hexan-1-ols Mediated by AllylSmBr
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-06-26 00:00:00 , DOI: 10.1021/acs.joc.8b01170 Xiaoxia Wang 1, 2 , Jianyong Li 2 , Ting Yuan 2 , Bingxin You 2 , Guanqun Xie 1, 2 , Xin Lv 2
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-06-26 00:00:00 , DOI: 10.1021/acs.joc.8b01170 Xiaoxia Wang 1, 2 , Jianyong Li 2 , Ting Yuan 2 , Bingxin You 2 , Guanqun Xie 1, 2 , Xin Lv 2
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The selective construction of bicyclo[3.3.0]octan-1-ols and bicyclo[3.1.0]hexan-1-ols was achieved by using an allylSmBr/additive(s) system. By employing HMPA as the only additive, the momoallylation/ketone–alkene coupling occurred preferably and afforded bicyclo[3.3.0]octan-1-ols in good yields with high diastereoselectivities. While the ester–alkene coupling predominated to generate bicyclo[3.1.0]hexan-1-ols in moderate yields with excellent diastereoselectivities in the presence of a proton source, such as pyrrole as the coadditive with HMPA. The tunable reactivity of allylSmBr by additive(s) would make it a versatile reagent in organic synthesis.
中文翻译：
烯丙基SmBr介导的双环[3.3.0]辛烷-1-醇和双环[3.1.0]己-1-醇的加成调谐选择性合成
通过使用烯丙基SmBr /添加剂系统，可以选择性地构建双环[3.3.0]辛烷-1-醇和双环[3.1.0]己-1-醇。通过采用HMPA作为唯一的添加剂，优选发生甲代烯丙基化/酮-烯烃偶联，并以高收率和高非对映选择性提供双环[3.3.0] octan-1-ol。在质子源（例如吡咯与HMPA共存）存在下，酯-烯烃偶联主要以中等收率产生双环[3.1.0]己-1-醇，具有非对映选择性。添加剂对烯丙基SmBr的可调反应性使其成为有机合成中的通用试剂。
更新日期：2018-06-26
中文翻译：
烯丙基SmBr介导的双环[3.3.0]辛烷-1-醇和双环[3.1.0]己-1-醇的加成调谐选择性合成
通过使用烯丙基SmBr /添加剂系统，可以选择性地构建双环[3.3.0]辛烷-1-醇和双环[3.1.0]己-1-醇。通过采用HMPA作为唯一的添加剂，优选发生甲代烯丙基化/酮-烯烃偶联，并以高收率和高非对映选择性提供双环[3.3.0] octan-1-ol。在质子源（例如吡咯与HMPA共存）存在下，酯-烯烃偶联主要以中等收率产生双环[3.1.0]己-1-醇，具有非对映选择性。添加剂对烯丙基SmBr的可调反应性使其成为有机合成中的通用试剂。
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