School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Org Lett. 2010 Dec 3;12(23):5442-5. doi: 10.1021/ol102155h. Epub 2010 Nov 9.
On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control.
用氨基锂进行锂化反应时，N-烯丙基-N'-芳基脲发生重排，芳基从 N 原子转移到烯丙基的α-碳原子上。在手性氨基锂的影响下，从α-芳基化产物中进一步进行芳基转移，可以对 1,1-二芳基烯丙基胺衍生物进行对映选择性构建。这些反应的立体选择性源于动力学控制下平面手性烯丙基锂的对映选择性形成。
