Asymmetric transfer hydrogenation of cyclic imines in water with a versatile hydrogen donorformic acid/N-methylpiperidine: rapid access to highly enantioselective amines

TitleAsymmetric transfer hydrogenation of cyclic imines in water with a versatile hydrogen donorformic acid/N-methylpiperidine: rapid access to highly enantioselective amines
Publication TypeJournal Article
Year of Publication2016
AuthorsShende, VS, Shingote, SK, Deshpande, SH, Kelkar, AA
JournalChemistryselect
Volume1
Issue10
Pagination2221-2224
Date PublishedJUL
Abstract

Asymmetric transfer hydrogenation (ATH) of cyclic imines in water has been investigated for the first time by using HCOOH in combination with bases other than triethylamine as H donor. Effect of FA/Base ratio has shown significant impact on activity and enantioselectivity for ATH reaction in water. Use of methanol as a co-solvent improved the reduction performance. FA/N-methylpiperidine was found to be excellent, versatile hydrogen donor for ATH of imine 6,7-dimethoxy-1-methyl-3,4-dihy-droisoquinoline (1a) giving by far the highest noted TOF value of 5940 h(-1). ATH of-different imines derivatives including 3, 4-dihydoisoquinolines, beta-carbolines and cyclic sulfonyl imines have been performed with excellent activity (91-99% yield) and enantioselectivity (88-97%) in very short time (1-2 min). This is very simple protocol for rapid access to enantioselective amines with very new and versatile hydrogen donor 1.1 FA/Nmethylpiperidine.

DOI10.1002/slct.201600497
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

0.00

Divison category: 
Chemical Engineering & Process Development