Asymmetric hydrogenation of heteroaromatic ketones and cyclic and acyclic enones mediated by Cu(I)-chiral diphosphine catalysts

Hideo Shimizu, Takuto Nagano, Noboru Sayo, Takao Saito, Takashi Ohshima, Kazushi Mashima

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Copper(I)-catalyzed asymmetric hydrogenation of heteroaromatic ketones, cyclic and acyclic enones is reported. The choice of the chiral diphosphine ligand highly influenced enantiose-lectivity as well as chemoselectivity. Highly enantioselective hydrogenation of ortho-substituted heteroaromatic ketones was achieved using BDPP as the ligand. In the 1,2-selective hydrogenation of acylic enone, SEGPHOS gave higher enantioselectivity than BDPP. On the other hand, the bulky ligand DTBM-SEGPHOS had a 1,4-selective nature, leading to the first highly 1,4-selective and enantioselective hydrogenation of cyclic enones.

Original languageEnglish
Pages (from-to)3143-3146
Number of pages4
JournalSynlett
Issue number19
DOIs
Publication statusPublished - Dec 21 2009
Externally publishedYes

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Ketones
Hydrogenation
Catalysts
Ligands
Enantioselectivity
Copper

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Asymmetric hydrogenation of heteroaromatic ketones and cyclic and acyclic enones mediated by Cu(I)-chiral diphosphine catalysts. / Shimizu, Hideo; Nagano, Takuto; Sayo, Noboru; Saito, Takao; Ohshima, Takashi; Mashima, Kazushi.

In: Synlett, No. 19, 21.12.2009, p. 3143-3146.

Research output: Contribution to journalArticle

Shimizu, Hideo ; Nagano, Takuto ; Sayo, Noboru ; Saito, Takao ; Ohshima, Takashi ; Mashima, Kazushi. / Asymmetric hydrogenation of heteroaromatic ketones and cyclic and acyclic enones mediated by Cu(I)-chiral diphosphine catalysts. In: Synlett. 2009 ; No. 19. pp. 3143-3146.
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