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Synfacts 2022; 18(04): 0406
DOI: 10.1055/s-0041-1737959
Metals in Synthesis

The Fukuyama Reduction of Thio Esters to Aldehydes

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Phillip Pommerening
Fukuyama T, *, Lin S.-C, Li L. Rice University, Houston, USA
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.
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Key words

aldehydes - hydrosilane - palladium catalysis - reduction - thio esters

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.


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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.


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Publication History

Article published online:
18 March 2022

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