Organocatalytic Mukaiyama Mannich Reactions of 2,5-Bis(trimethylsilyloxy)furan
Organocatalytic Mukaiyama Mannich Reactions of 2,5-Bis(trimethylsilyloxy)furan
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DOI：
10.1021/acs.orglett.9b01664
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发表时间：
2019-07-05
期刊：
影响因子：
5.2
通讯作者：
Shaw, Jared T.
中科院分区：
文献类型：
--
作者：
Laws, Stephen W.;Howard, Sara Y.;Shaw, Jared T.
本文描述了2，5-双(三甲基硅氧基)呋喃与亚胺的Mukaiyama Mannich加成反应合成密集取代的单、双伽马-内酰胺的有机催化合成方法。使用二苯磺酰亚胺催化剂通过单加成生产伽马-内酰胺，而更酸性的催化剂(三氟酸)通过双重加成生产熔融双内酰胺。优化的有机催化条件允许选择性地合成所需的核以及由醛、胺和双三甲基硅氧基呋喃合成的三取代单内酰胺的一锅多组分组装。对手性酸的研究发现，这些有机催化剂在单加成反应中具有高度的活性和非对映选择性，尽管没有对映体选择性。
The organocatalytic synthesis of densely substituted mono- and bis-gamma-lactams involving the Mukaiyama Mannich addition of 2,5-bis(trimethylsilyloxy)furan to imines is described. Use of a ditoluenesulfonylimide catalyst produces gamma-lactams from monoaddition, whereas a more acidic catalyst (triflic acid) produces fused bis-lactams from double addition. Optimized organocatalytic conditions allow for the selective synthesis of either desired core as well as the one-pot, multicomponent assembly of the trisubstituted monolactams from aldehydes, amines, and bis-trimethylsilyloxyfuran. An examination of chiral acids found these organocatalysts to be highly active and diastereoselective in the monoaddition reaction, albeit with no enantioselectivity.