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2.5.1.1.2 Hydrogenation of Optically Active Esters

DOI: 10.1055/sos-SD-227-00090

Shi, Y.; Cole-Hamilton, D. J.; Kamer, P. C. J.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (20182200.

Ruthenium complex 23 is a highly active catalyst for ester hydrogenation.[‌39‌] Kuriyama and co-workers tested its activity for optically active esters in 2010.[‌46‌] Unfortunately, there is a substantial loss in enantiomeric excess during the hydrogenation reaction [62% Δee for methyl (S)-2-methyl-3-phenylpropanoate]. Screening of diamine and bisphosphine ligands with the [RuCl2(bisphosphine)(diamine)] precursor suggested that 1,3-bis(diphenylphosphino)propane (dppp) together with 1,2-diphenylethylene-1,2-diamine (dpen) has the best performance. Complexes (R,R)-36 and (S,S)-36 (Scheme 14) were therefore developed for the hydrogenation of chiral esters, with the corresponding alcohols obtained in high yield with no loss of optical purity (Table 2).

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8 (M,M)-88 88 (<8) [‌88‌]
8 (M,M)-88 88 (8) [‌88‌]
8 (M,M)-88 88 (8) [‌88‌]
8 (M,M)-88 88 (<8) [‌88‌]
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8 (M,M)-88 8e [‌88‌]
8 (M,M)-88 88e (<8) [‌88‌]
8 (M,M)-88 88e (<8) [‌88‌]
8 (M,M)-88 88 (88) [‌88‌]
88 (M,M)-88 88 (88) [‌88‌]
88 (M,M)-88 88 (<8) [‌88‌]
88 (M,M)-88 88 (<8) [‌88‌]

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