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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

Authors

    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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Further Information

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.


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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