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
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).
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.
