Chiral sulfur compounds. 7. Stereoselective reactions of lithium and zinc tert-butyl phenylmethyl sulfoxide with carbonyl compounds and imines
Chiral sulfur compounds. 7. Stereoselective reactions of lithium and zinc tert-butyl phenylmethyl sulfoxide with carbonyl compounds and imines
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手性硫化合物。
DOI：
10.1021/jo00272a040
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发表时间：
1989
影响因子：
3.6
通讯作者：
G. Boche
中科院分区：
文献类型：
--
作者：
S. Pyne;G. Boche
用二苯甲酮猝灭外消旋叔丁基苯基甲基亚磺酸锂1A，经单晶X-射线分析确定为Cñ，S，-2-(叔丁基亚磺基)-1，1，2-三苯基乙醇。报道了1A与各种醛和亚胺反应中的非对映选择性与醛、亚胺结构和金属阳离子(Li+或Zn2+)的关系。两种底物都表现出对非对映选择的偏好。过渡态结构被提出来解释这一非对映选择。
Racemic lithium tert-butyl phenylmethyl sulfoxide 1A when quenched with benzophenone gives Cñ, Sñ,-2-(tert-butylsulfinyl)-1, 1, 2-triphenylethanol as determined by single-crystal X-ray analysis. The diastereoselection in the reaction of 1A with various aldehydes and imines as a function of aldehyde and imine structure and metal cation (Li+ or Zn2+) is reported. Both substrates show a preference foranti diastereoselection. Transition-state structures are proposed to account forthis diastereoselection.