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Synfacts 2016; 12(2): 0153
DOI: 10.1055/s-0035-1561196
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Azides and Nitriles in Palladium-Catalyzed Decarboxylative Allylation

Contributor(s):
Mark Lautens
,
Thomas Johnson
Vita MV, Caramenti P, Waser J * École Polytechnique Fédérale de Lausanne, Switzerland
Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation.

Org. Lett. 2015;
17: 5832-5835
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Publication History

Publication Date:
19 January 2016 (online)

 
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Key words

allylic alkylation - palladium - azides - nitriles

Significance

Homoallylic azides and cyanides are synthesized in enantioenriched form through a palladium-catalyzed decarboxylative allylation on indanones. These functional groups had seen little (CN) to no (N3) reported use in the title reaction.


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Comment

The products are obtained in very good yield and mostly with high enantioselectivity. The starting materials can be synthesized in one step from the corresponding β-keto esters using hypervalent iodine reagents developed in the authors’ laboratories.


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