An efficient approach to the multigram synthesis of 3‐azabicyclo[3.1.1]heptanes is described. The method relied on the intramolecular imide formation in the properly 1,3‐functionalized cyclobutane derivative. In turn, the latter compound was obtained via the diastereoselective Strecker reaction of readily accessible 3‐oxo­cyclobutanecarboxylate. The resulting synthetic intermediate – 1‐amino‐3‐azabicyclo[3.1.1]heptane‐2,4‐dione – was used to synthe­size several monoprotected bicyclic diamines valuable as building blocks for medicinal chemistry, as well as a series of bridged analogs of Thalidomide, a known anticancer drug and a component of proteolysis‐targeting chimeras (PROTACs).

中文翻译：

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3-氮杂双环[3.1.1]庚烷衍生物的多克合成，包括双环沙利度胺类似物


描述了一种 3-氮杂双环 [3.1.1] 庚烷多克合成的有效方法。该方法依赖于适当 1,3-官能化的环丁烷衍生物中的分子内酰亚胺形成。反过来，后一种化合物是通过易于获得的 3-氧代环丁烷羧酸盐的非对映选择性 Strecker 反应获得的。所得合成中间体 – 1-氨基-3-氮杂双环[3.1.1]庚烷-2,4-二酮 - 用于合成几种单保护双环二胺，这些二胺作为药物化学的组成部分，以及沙利度胺的一系列桥式类似物，沙利度胺是一种已知的抗癌药物和蛋白水解靶向嵌合体 （PROTAC） 的组成部分。