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Literature DB >> 17444684

Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines.

You-Qing Wang¹, Sheng-Mei Lu, Yong-Gui Zhou.

Abstract

Pd/bisphosphines complexes are highly effective catalysts for asymmetric hydrogenation of activated imines in trifluoroethanol. The asymmetric hydrogenation of N-diphenylphosphinyl ketimines 3 with Pd(CF3CO2)/(S)-SegPhos indicated 87-99% ee, and N-tosylimines 5 could gave 88-97% ee with Pd(CF3CO2)/(S)-SynPhos as a catalyst. Cyclic N-sulfonylimines 7 and 11 were hydrogenated to afford the useful chiral sultam derivatives in 79-93% ee, which are important organic synthetic intermediates and structural units of agricultural and pharmaceutical agents.

Entities: Chemical

Year: 2007 PMID： 17444684 DOI： 10.1021/jo0700878

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

4 in total

1. Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

Authors: Wenhua Ou; Sandraliz Espinosa; Héctor J Meléndez; Silvia M Farré; Jaime L Alvarez; Valerie Torres; Ileanne Martínez; Kiara M Santiago; Margarita Ortiz-Marciales
Journal: J Org Chem Date: 2013-05-13 Impact factor: 4.354

Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines.

1. Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

2. Pd(OAc)₂-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

3. Self-Suspended Nanoparticles for N-Alkylation Reactions: A New Concept for Catalysis.

4. Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines.

Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines.

1. Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

2. Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

3. Self-Suspended Nanoparticles for N-Alkylation Reactions: A New Concept for Catalysis.

4. Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines.

2. Pd(OAc)₂-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.