Dual-organocatalyst-promoted asymmetric cascade reaction: highly efficient construction of enantiopure fully substituted tetrahydro-1,2-oxazines.
Dual-organocatalyst-promoted asymmetric cascade reaction: highly efficient construction of enantiopure fully substituted tetrahydro-1,2-oxazines.
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DOI：
10.1021/ol403463h
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发表时间：
2014-01
期刊：
影响因子：
5.2
通讯作者：
Hua-Chen Lin;Xingwen Sun;G. Lin
中科院分区：
文献类型：
--
作者：
Hua-Chen Lin;Xingwen Sun;G. Lin
采用四组分不对称α-氨氧基化/aza-Michael/Mannich级联反应，在温和条件下，以高收率和良好的对映体和非对映体选择性合成了全取代的手性四氢-1，2-恶嗪衍生物.该1，2-恶嗪衍生物可通过N-O断裂和稠合三环4-氨基取代四氢喹啉以良好的产率转化为相应的多官能手性氨基醇，随后进行Friedel-Crafts反应，具有良好的立体选择性。通过4-氨基取代的四氢喹啉的C-4转化也获得了4-烷氧基取代的四氢喹啉。
A four-component asymmetric α-aminoxylation/aza-Michael/Mannich cascade reaction for the construction of fully substituted chiral tetrahydro-1,2-oxazine derivatives was accomplished in high yields with excellent enantio- and diastereoselectivities under mild conditions. The 1,2-oxazine derivative could be transformed to the corresponding multifunctional chiral amino alcohol by N-O cleavage and fused-tricyclic 4-amino-substituted tetrahydroquinolines in good yields with excellent stereoselectivities followed by a Friedel-Crafts reaction. Also a 4-alkoxy-substituted tetrahydroquinoline was achieved by C-4 inversion of a 4-amino-substituted tetrahydroquinoline.