Wangweerawong Apiwat, Bergman Robert G, Ellman Jonathan A
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
J Am Chem Soc. 2014 Jun 18;136(24):8520-3. doi: 10.1021/ja5033452. Epub 2014 Jun 5.
The first asymmetric intermolecular addition of non-acidic C-H bonds to imines is reported. The use of the activating N-perfluorobutanesulfinyl imine substituent is essential for achieving sufficient reactivity and provides outstanding diastereoselectivity (>98:2 dr). Straightforward removal of the sulfinyl group with HCl yields the highly enantiomerically enriched amine hydrochlorides.
报道了首例非酸性C-H键与亚胺的不对称分子间加成反应。使用活化的N-全氟丁烷亚磺酰亚胺取代基对于实现足够的反应活性至关重要,并提供了出色的非对映选择性(>98:2 dr)。用盐酸直接去除亚磺酰基,得到高度对映体富集的胺盐酸盐。