Secondary amines as coupling partners in direct catalytic asymmetric reductive amination Electronic supplementary information (ESI) available: Procedures and spectra

The secondary amine participating asymmetric reductive amination remains an unsolved problem in organic synthesis. Here we show for the first time that secondary amines are capable of effectively serving as N-sources in direct asymmetric reductive amination to afford corresponding tertiary chiral am...

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Published inChemical science (Cambridge) Vol. 10; no. 16; pp. 4509 - 4514
Main Authors Wu, Zitong, Du, Shaozhi, Gao, Guorui, Yang, Wenkun, Yang, Xiongyu, Huang, Haizhou, Chang, Mingxin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.04.2019
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ENANTIOSELECTIVE HYDROGENATION
ALKYL-ARYL KETONES
IDENTIFICATION
IR-F-BINAPHANE
SALTS
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Summary:The secondary amine participating asymmetric reductive amination remains an unsolved problem in organic synthesis. Here we show for the first time that secondary amines are capable of effectively serving as N-sources in direct asymmetric reductive amination to afford corresponding tertiary chiral amines with the help of a selected additive set under mild conditions (0-25 degrees C). The applied chiral phosphoramidite ligands are readily prepared from BINOL and easily modified. Compared with common tertiary chiral amine synthetic methods, this procedure is much more concise and scalable, as exemplified by the facile synthesis of rivastigmine and N-methyl-1-phenylethanamine.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc00323a