Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts
Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts
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DOI：
10.1002/adsc.202000227
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发表时间：
2020-04-23
影响因子：
5.4
通讯作者：
Zhao, John C. -G.
中科院分区：
文献类型：
--
作者：
Jakkampudi, Satish;Konda, Swapna;Zhao, John C. -G.
通过使用适当的模块化设计的有机催化剂（MDO），由氨基酸和金鸡纳生物碱衍生物原位自组装，实现了桥连1，2，3，4-四氢异喹啉衍生物的非对映异构合成。（E）-2-[2-（3-芳基-3-氧代丙-1-烯-1-基）苯基]乙醛与（E）-2-[（4-甲氧基苯基）亚氨基]乙酸乙酯或苄酯在MDO催化下的多米诺Mannich/aza-Michael/aldol反应以良好的产率和优异的非对映选择性（高达99：1dr）和对映选择性（高达> 99%ee）得到所需桥连四氢异喹啉的两种不同非对映体。在羟醛缩合反应步骤中实现非对映异构。
The diastereodivergent synthesis of bridged 1,2,3,4-tetrahydroisoquinoline derivatives has been achieved by using appropriate modularly designed organocatalysts (MDOs) that are self-assembled in situ from amino acids and cinchona alkaloid derivatives. The domino Mannich/aza-Michael/aldol reaction between (E)-2-[2-(3-aryl-3-oxoprop-1-en-1-yl)phenyl]acetaldehydes and ethyl or benzyl (E)-2-[(4-methoxyphenyl)imino]acetates catalyzed by MDOs gives two different diastereomers of the desired bridged tetrahydroisoquinolines in good yields and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to >99% ee). The diastereodivergence was achieved in the aldol reaction step.