一、Cram规则:
此规则由Donald J. Cram在1952年提出【J. Am. Chem. Soc. 1952, 74, 5828; 5851】,解释和预测亲核试剂对α-手性醛酮加成的立体选择性。RL, RM, Rs 三个基团分别代表α-碳原子上连接的大、中、小( 体积) 原子( 基团)。Cram认为,进攻试剂Nu对羰基加成的第一步就是其金属部分先与羰基氧原子配位,加大了氧原子一端的体积,使之定位于RM和Rs之间,即反应物的优势构象为RL与羰基处于对位交叉式,加成的第二步即亲核试剂向Rs侧进攻最为有利,Cram规则。
规则特点:
1、α-手性碳上带有“RL, RM, Rs” 三个基团,在纽曼投影式中RL与羰基处于对位交叉式。
2、亲核试剂Nu从空间位阻更小的Rs一侧进攻。
二、Felkin-Anh规则:
此规则是对Cram规则的发展,1968年,Felkin提出了另一规则,而后Anh在量化计算和考虑Burgi-Dunitz轨道角的基础上修正了Felkin规则,后被称为Felkin-Anh规则【Top. Curr. Chem. 1980, 88, 145】。现在Felkin-Anh规则已经成为解释和预测亲核试剂对α-手性醛酮加成的立体选择性的最常用规则。
规则特点:
1、RL与羰基处于垂直交叉式。
2、亲核试剂从空间位阻更小的Rs一侧进攻。
3、亲核试剂从符合Burgi-Dunitz轨道角(107°)(点击查看详细介绍)的方向进攻。
根据Burgi-Dunitz轨道角亲核试剂从羰基107°方向进攻,上图构象刚好在Rs一侧进攻,此方向进攻得到的产物为主要产物。
此构象从Burgi-Dunitz轨道角方向进攻,处于RM位置进攻,位阻较大,此产物为次要产物。
三、Cram螯合规则:
α-手性碳上带有好的螯合基团(OR, NR2, SR)时,在好的螯合金属(Li+,MgX+, ZnCl2,TiCl4,MgCl2)存在下,作为Lewis酸的螯合金属和羰基络合的同时也和作为Lewis碱的螯合基团进行络合形成了一个环状结构。
规则特点:
1、螯合基团与羰基处于重叠交叉式,在螯合金属的络合下形成环状结构。
2、亲核试剂从空间位阻更小的Rs一侧进攻。
当Lewis酸和Lewis碱同时存在,满足Cram螯合规则条件时,会形成环状过渡态,Felkin-Anh规则不适用。
参考文献
一、《有机人名反应、试剂与规则》,黄培强等编著,P410-413。
二、https://www.bilibili.com/video/av201367616/
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