Enantioselective organocatalytic α-fluorination of aldehydes
Enantioselective organocatalytic α-fluorination of aldehydes
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DOI：
10.1021/ja051805f
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发表时间：
2005-06-22
影响因子：
15
通讯作者：
MacMillan, DWC
中科院分区：
文献类型：
--
作者：
Beeson, TD;MacMillan, DWC
醛的第一个直接对映选择性催化α-氟化已经完成。烯胺催化的使用为醛的对映选择性氟化生成α-氟醛提供了一种新的有机催化策略，α-氟醛是药物合成中重要的手性合成子。已发现使用咪唑啉酮 1 作为不对称催化剂可以介导多种醛底物的氟化，而 N-氟苯磺酰亚胺作为氟的亲电子源。这种新的有机催化转化还可以适应多种醛底物。虽然本研究中通常使用 20 mol% 的催化剂量，但使用低至 2.5 mol% 的催化剂负载量即可成功卤化。
The first direct enantioselective catalytic alpha-fluorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective fluorination of aldehydes to generate a-fluoro aldehydes, an important chiral synthon for medicinal agent synthesis. The use of imidazolidinone 1 as the asymmetric catalyst has been found to mediate the fluorination of a large variety of aldehyde substrates with N-fluorobenzenesulfonimide serving as the electrophilic source of fluorine. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 20 mol % were generally employed in this study, successful halogenation can be accomplished using catalyst loadings as low as 2.5 mol %.