期刊
NATURE CATALYSIS
卷 1, 期 8, 页码 601-608出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/s41929-018-0111-8
关键词
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资金
- National Key Research and Development Program of China [2016YFA0202900]
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Natural Science Foundation of China [21332009, 21572252]
- Strategic Priority Research Program [XDB20000000]
- Key Research Program of Frontier Sciences of the Chinese Academy of Sciences [QYZDYSSWSLH012]
- Science and Technology Commission of Shanghai Municipality [16XD1404300]
Prenylation is a ubiquitous process common to almost all living organisms, and a key transformation in organic synthesis. Dearomative prenylation reactions of tryptophan derivatives lead to various prenylated indoline alkaloids with diverse biological activities. However, enantioselective dearomative prenylations without a pre-installed stereogenic centre in the substrate have not been reported. Here, we show that a small molecule-based catalytic system derived from a commercially available palladium precursor and a chiral phosphoramidite ligand (allylphos) can catalyse the enantioselective dearomative prenylation of indole derivatives, which tolerates a much broader substrate scope than those of known enzymatic dearomative prenylation processes. Enantioselective dearomative geranylation and farnesylation reactions also proceed smoothly under the standard conditions. The concise total or formal syntheses of a series of natural products can be realized using this catalytic system. The mechanistic investigations provide deep insights for the further design of chiral ligands and catalysts for asymmetric reactions.
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