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Intermolecular Rhodium(II)‐Catalyzed Allylic C( sp 3 )–H Amination of Cyclic Enamides
Author(s) -
ReyRodriguez Romain,
Jestin Grégory,
Gandon Vincent,
Grelier Gwendal,
Retailleau Pascal,
Darses Benjamin,
Dauban Philippe,
Gillaizeau Isabelle
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701188
Subject(s) - amination , chemistry , allylic rearrangement , rhodium , chemoselectivity , intermolecular force , catalysis , medicinal chemistry , combinatorial chemistry , functional group , stereochemistry , organic chemistry , molecule , polymer
The intermolecular rhodium(II)‐catalyzed C( sp 3 )–H amination of enamides gives access to new 4‐aminopiperidine derivatives that are useful building blocks in medicinal chemistry. This efficient transformation proceeds at room temperature with complete regio‐ and chemoselectivity in favor of the allylic C( sp 3 )–H bond, and has a broad functional group tolerance. In addition, the matched combination of the chiral complex Rh 2 ( S ‐nta) 4 [nta=( S )‐ N ‐1,8‐naphthoylalanine] with an optically pure ( S )‐sulfonimidamide allows the isolation of allylic amines with excellent stereocontrol.