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Sc(OTf)3-Catalyzed Addition of Bromomagnesium 2-Vinyloxy Ethoxide to Various Aldehydes Leading to Protected Aldol Products

Pauline Quinio, Laura Kohout, Daniela Sustac Roman, Jakob Gaar, Konstantin Karaghiosoff, Paul Knochel*

*Ludwig Maximilians-University Munich, Department of Chemistry, Butenandtstrasse 5-13, 81377 München, Germany, Email: paul.knochelcup.uni-muenchen.de

P. Quinio, L. Kohout, D. S. Roman, J. Gaar, K. Karahiosoff, P. Knochel, Synlett, 2016, 27, 1715-1719.

DOI: 10.1055/s-0035-1561934 (free Supporting Information)


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Abstract

The addition of bromomagnesium 2-vinyloxy ethoxide to various aldehydes in the presence of 10 mol% Sc(OTf)3 provides a broad range of functionalized protected aldol compounds. A Swern oxidation-CBS reduction sequence enables the preparation of chiral protected aldol products.

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Key Words

β-hydroxy aldehydes, 1,3-dioxolanes, Grignard addition, scandium triflate, catalysis


ID: J60-Y2016