Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721 302, India.
J Org Chem. 2011 Sep 16;76(18):7334-40. doi: 10.1021/jo200711s. Epub 2011 Aug 12.
Catalytic enantioselective one-pot aziridoarylation reaction of aryl cinnamyl ethers has been demonstrated in detail. Combination of suitable copper catalyst and chiral bis-oxazoline ligand was found to be very efficient for asymmetric aziridination followed by intramolecular arylation (Friedel-Crafts) reaction to provide a general and direct method for the synthesis of trans-3-amino-4-arylchromans with high regio-, diastereo- (dr > 99:1), and enantioselectivity (up to 95% ee) with moderate yield. trans-3-Amino-4-arylchroman is an advanced intermediate for the synthesis of chromenoisoquinoline compounds such as doxanthrine, a potent and selective full agonist for the dopamine-D(1) receptor.
详细展示了芳基肉桂基醚的催化对映选择性一锅法叠氮芳基化反应。合适的铜催化剂和手性双恶唑啉配体的组合对于不对称氮丙啶化反应非常有效，随后进行分子内芳基化（傅克反应）反应，为反式-3-氨基-4-芳基色满的合成提供了一种通用且直接的方法，具有高区域选择性、非对映选择性（dr>99:1）和对映选择性（高达 95%ee），产率适中。反式-3-氨基-4-芳基色满是合成色满异喹啉化合物如 doxanthrine 的重要中间体， doxanthrine 是多巴胺-D(1)受体的有效和选择性完全激动剂。
