Tandem-Directed Regioselective
Hydroformylation/β-Elimination: A Practical
Method for the Synthesis of Enals

Achim Bruch; Antje Gebert; Bernhard Breit

doi:10.1055/s-2008-1067140

PAPER

Tandem-Directed Regioselective Hydroformylation/β-Elimination: A Practical Method for the Synthesis of Enals

Achim Bruch, Antje Gebert, Bernhard Breit*
Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104 Freiburg i. Breisgau, Germany
Fax: +49(761)2038715; e-Mail: bernhard.breit@organik.chemie.uni-freiburg.de;

Abstract

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Abstract

A practical synthesis of α,β-unsaturated aldehydes by a tandem-directed hydroformylation/β-elimination process of allylic o-DPPB esters is reported. The o-DPPB group served as an effective controller for regioselectivity of the hydroformylation towards the desired aldolate isomer, and was subsequently eliminated in situ by mild standard bases. The reaction is rather general for the preparation of 1,1-disubstituted and trisubstituted enals and is compatible with many functional groups. Recovery of the o-DPPBA is possible either by chromatography or precipitation as the diethylammonium salt.

Key words

hydroformylation - enals - tandem reaction - aldehydes - rhodium

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