Malpass John R, Handa Sandeep, White Richard
Department of Chemistry, University of Leicester, Leicester LE1 7RH, United Kingdom.
Org Lett. 2005 Jun 23;7(13):2759-62. doi: 10.1021/ol0510365.
[reaction: see text] Coupling of N-Boc-7-bromo-2-azabicyclo[2.2.1]heptane with aryl and pyridyl boronic acids incorporates aryl and heterocyclic substituents at the 7-position and leads to a preference for syn over anti stereoisomers. Incorporation of a chloropyridyl group followed by N-deprotection gives syn-isoepibatidine. Facial selectivity in attack on 7-keto-2-azanorbornanes depends heavily on the N-protecting group leading to the first syn-7-hydroxy-2-azabicyclo[2.2.1]heptane derivative.
[反应：见正文] N-叔丁氧羰基-7-溴-2-氮杂双环[2.2.1]庚烷与芳基硼酸和吡啶硼酸的偶联反应在7位引入芳基和杂环取代基，并导致顺式立体异构体比反式立体异构体更受青睐。引入氯吡啶基然后进行N-脱保护得到顺式异埃博霉素。对7-酮-2-氮杂降冰片烷的进攻中的面选择性很大程度上取决于N-保护基，从而得到第一个顺式-7-羟基-2-氮杂双环[2.2.1]庚烷衍生物。
