Asymmetric transfer hydrogenation of imines in water by varying the ratio of formic acid to triethylamine

TitleAsymmetric transfer hydrogenation of imines in water by varying the ratio of formic acid to triethylamine
Publication TypeJournal Article
Year of Publication2015
AuthorsShende, VS, Deshpande, SH, Shingote, SK, Joseph, A, Kelkar, AA
JournalOrganic Letters
Volume17
Issue12
Pagination2878-2881
Date PublishedJUN
ISSN1523-7060
Abstract

Asymmetric transfer hydrogenation (ATH) of imines has been performed with variation in formic acid (F) and triethylamine (T) molar ratios in water. The F/T ratio is shown to affect both the reduction rate and enantioselectivity, with the optimum ratio being 1.1 in the ATH of imines with the Rh-(1S,2S)-TsDPEN catalyst. Use of methanol as a cosolvent enhanced reduction activity. A variety of imine substrates have been reduced, affording high yields (94-98%) and good to excellent enantioselectivities (89-98%). In comparison with the common azeotropic F-T system, the reduction with 1.1/1 F/T is faster.

DOI10.1021/acs.orglett.5b00889
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.732

Divison category: 
Chemical Engineering & Process Development