Denolf Bram, Mangelinckx Sven, Törnroos Karl W, De Kimpe Norbert
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Org Lett. 2007 Jan 18;9(2):187-90. doi: 10.1021/ol0622054.
Treatment of novel chiral N-sulfinyl alpha-chloro ketimines with Grignard reagents resulted in the synthesis of chiral N-(1-substituted cyclopropyl)-tert-butanesulfinamides in acceptable to good yields and diastereoselectivity via 1,3-dehydrohalogenation and subsequent addition of the Grignard reagent to the intermediate cyclopropylideneamine. Only in the case of allylmagnesium chloride did the reaction lead to aziridines in high yield. Further deprotection toward N-unprotected 1-substituted cyclopropylamines was established, and the absolute configuration was determined. [reaction: see text].
用格氏试剂处理新型手性 N-亚磺酰基α-氯代酮亚胺，通过 1,3-脱卤化氢反应以及随后格氏试剂加成到中间体环亚丙基胺上，以可接受的良好产率和非对映选择性合成了手性 N-(1-取代环丙基)-叔丁基亚磺酰胺。仅在烯丙基氯化镁的情况下，反应才能高产率地生成氮丙啶。建立了进一步脱保护生成 N-未保护的 1-取代环丙胺的方法，并确定了绝对构型。[反应：见正文]
