Diastereoselective Nickel-Catalyzed Reductive Couplings of Aminoaldehydes and Alkynylsilanes: Application to the Synthesis of D-erythro-Sphingosine.

Tetrahedron
Kanicha Sa-Ei, John Montgomery

Abstract

A strategy for the nickel-catalyzed reductive coupling of α-aminoaldehydes with silyl alkynes has been developed. The process proceeds with exceptional regiocontrol and diastereoselectivity. A variety of protected serinal derivatives were examined, and Garner aldehyde afforded the highest chemical yields of an easily deprotected coupling product. Use of a C-15 alkyne allowed a direct and efficient synthesis of D-erythro-sphingosine. With this silyl alkyne of interest, coupling reactions were most efficient when trace water was employed with THF as solvent. Using this procedure, D-erythro-sphingosine was prepared by a short sequence, wherein the alkene stereochemistry, C-3 stereocenter, and the C-3-C-4 carbon-carbon bond were all efficiently installed by the key nickel-catalyzed coupling process.

References

May 27, 2004·Organic & Biomolecular Chemistry·Staffan Torssell, Peter Somfai

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Citations

Sep 6, 2011·Organic Letters·María MorenoAntoni Riera
Apr 3, 2013·The Journal of Organic Chemistry·Daniel R FandrickChris H Senanayake
Oct 22, 2016·Tetrahedron·Natasha F O'RourkeGlenn C Micalizio
Feb 24, 2017·Beilstein Journal of Organic Chemistry·Hisashi MasuiTakashi Takahashi
Dec 25, 2013·Beilstein Journal of Organic Chemistry·Mikko Passiniemi, Ari Mp Koskinen
Jun 4, 2019·Chemical & Pharmaceutical Bulletin·Noriki KutsumuraTakao Saito

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