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DOI: 10.1055/s-0041-1737959
The Fukuyama Reduction of Thio Esters to Aldehydes
Facile Reduction of Ethyl Thio Esters to Aldehydes: Application to a Total Synthesis of (+)-Neothramycin A Methyl Ether.
J. Am. Chem. Soc. 1990;
112: 7050-7051
DOI: 10.1021/ja00175a043
Significance
In 1990, Fukuyama and co-workers introduced a facile reduction method to transform ethyl thio esters into the corresponding aldehydes using catalytic amounts of palladium and triethylsilane as stoichiometric reducing agent. The mild reaction conditions, high chemoselectivity, and broad functional group tolerance are noteworthy features of the Fukuyama reduction.
Comment
The method also allows for converting optically active amino acids into their aldehydes without loss of stereo information. Mechanistic investigations support the shown catalytic cycle and rule out a pathway in which the hydrosilane is activated by oxidative addition to the palladium catalyst.
Publikationsverlauf
Artikel online veröffentlicht:
18. März 2022
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