Whitehead Daniel C, Yousefi Roozbeh, Jaganathan Arvind, Borhan Babak
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
J Am Chem Soc. 2010 Mar 17;132(10):3298-300. doi: 10.1021/ja100502f.
A reagent controlled organocatalytic enantioselective chlorolactonization reaction has been developed. Several 4-aryl pentenoic acids were cyclized in the presence of 0.1 equiv of (DHQD)(2)PHAL, employing various N-chlorinated hydantoins as the terminal chlorenium source. Ten examples are presented with selectivities ranging from 43 to 90% ee. This work represents the first example of an enantioselective reagent-controlled chlorolactonization that approaches synthetically useful enantioselectivities.
已开发出一种试剂控制的有机催化对映选择性氯代内酯化反应。在0.1当量的（DHQD）₂PHAL存在下，使用各种N-氯化乙内酰脲作为末端氯鎓源，使几种4-芳基戊烯酸环化。给出了10个例子，对映选择性范围为43%至90%ee。这项工作代表了对映选择性试剂控制的氯代内酯化反应的第一个例子，该反应接近具有合成实用性的对映选择性。
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