Everett Renata K, Wolfe John P
Department of Chemistry, University of Michigan , 930 N. University Avenue, Ann Arbor, Michigan 48109-1055, United States.
J Org Chem. 2015 Sep 18;80(18):9041-56. doi: 10.1021/acs.joc.5b01286. Epub 2015 Sep 1.
Treatment of N-(arylmethyl)-N-aryl or N-allyl-N-aryl glycine methyl ester derivatives with (n)Bu2BOTf and (i)Pr2NEt effects an aza-Wittig rearrangement that provides N-aryl phenylalanine methyl ester derivatives and N-aryl allylglycine methyl ester derivatives, respectively, in good yield with moderate to good diastereoselectivity. Under similar conditions, analogous substrates bearing N-carbonyl groups are converted to 1,4,2-oxazaborole derivatives. Additionally, N-allyl-N-aryl glycine methyl ester derivatives subjected to similar conditions at elevated temperatures undergo an aza-[2,3]-Wittig rearrangement, followed by a subsequent hydroboration oxidation reaction, to afford substituted amino alcohol products.
用二丁基三氟甲磺酸硼酯和二异丙基乙胺处理N-（芳基甲基）-N-芳基或N-烯丙基-N-芳基甘氨酸甲酯衍生物会引发氮杂维蒂希重排反应，分别以良好的产率和中等至良好的非对映选择性得到N-芳基苯丙氨酸甲酯衍生物和N-芳基烯丙基甘氨酸甲酯衍生物。在相似条件下，带有N-羰基的类似底物会转化为1,4,2-氧氮杂硼戊环衍生物。此外，N-烯丙基-N-芳基甘氨酸甲酯衍生物在高温下于相似条件下会发生氮杂-[2,3]-维蒂希重排反应，随后进行硼氢化氧化反应，得到取代氨基醇产物。
