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Synfacts 2015; 11(11): 1169
DOI: 10.1055/s-0035-1560686
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Asymmetric Carboamination of Alkenes

Contributor(s):
Hisashi Yamamoto
,
Ramesh C. Samanta
White DR, Hutt JT, Wolfe JP * University of Michigan, Ann Arbor, USA
Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.

J. Am. Chem. Soc. 2015;
137: 11246−11249
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Further Information

Publication History

Publication Date:
19 October 2015 (online)

 
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Key words

palladium - aminopalladation - stereoselectivity - carboamination - alkenes - aminoindanes

Significance

The authors presented an asymmetric alkene carboamination reaction that uses an external amine nucleophile. A combination of a palladium(II) salt and the (S)-t-BuPHOX ligand worked efficiently to deliver 2-aminoindane derivatives in high yields and excellent enantioselectivities (>98% ee).


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Comment

The intermolecular anti-aminopalladation with an external amine nucleophile is the major highlight of this work. This group previously reported an intramolecular anti-aminopalladation for the synthesis of cyclic sulfonamides (Chem. Eur. J. 2014, 20, 8782). A deuterium-labelling study supported the anti-aminopalladation pathway. The choice of the chiral ligand and nucleophile are crucial for high yields and selectivities.


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