Catalytic Enantioselective Aziridoarylation of Aryl Cinnamyl toward Synthesis of trans-3-Amino-4-arylchromans
Catalytic Enantioselective Aziridoarylation of Aryl Cinnamyl toward Synthesis of trans-3-Amino-4-arylchromans
复制标题
DOI：
10.1021/jo200711s
复制
发表时间：
2011-09-16
影响因子：
3.6
通讯作者：
Sinha, Debarshi
中科院分区：
文献类型：
--
作者：
Hajra, Saumen;Sinha, Debarshi
芳基肉桂基醚的催化对映选择性一锅氮杂环芳基化反应已被详细证明。研究发现，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和随后的分子内芳基化（Friedel-Crafts）反应非常有效，为合成具有高区域选择性、非对映选择性（dr > 99:1）和对映选择性（高达 95% cc）且产率适中的反式-3-氨基-4-芳基苯并二氢吡喃提供了通用且直接的方法。 trans-3-Amino-4-arylchroman 是合成色异喹啉化合物的高级中间体，例如多黄嘌呤，多巴胺-D(1) 受体的有效选择性完全激动剂。
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 enantio-selectivity (up to 95% cc) 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.