Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 37, Pages 12048-12052Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807610
Keywords
amines; asymmetric catalysis; C-H activation; carboxylic acids; rhodium
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Funding
- JSPS KAKENHI [JP15H05802]
- JSPS KAKENHI Grant [JP18H04637, JP17H03049, JP17K15417,, JP16F16409]
- JST ACT-C Grant [JPMJCR12Z6]
- Asahi Glass Foundation
- Naito Foundation
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Reported is an achiral (CpRhIII)-Rh-x/chiral carboxylic acid catalyzed asymmetric C-H alkylation of diarylmethanamines with a diazomalonate, followed by cyclization and decarboxylation to afford 1,4-dihydroisoquinolin-3(2H)-one. Secondary alkylamines as well as nonprotected primary alkylamines underwent the transformation with high enantioselectivities (up to 98.5:1.5 e.r.) by using a newly developed chiral carboxylic acid as the sole source of chirality to achieve enantioselective C-H cleavage by a concerted metalation-deprotonation mechanism.
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