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Literature DB >> 16144373

Enantioselective reduction of imines catalyzed by a rhenium(V)-oxo complex.

Kristine A Nolin¹, Richard W Ahn, F Dean Toste.

Abstract

An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)-oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium-oxo complex of the general formula (CNbox)Re(O)Cl2(OPPh3). Using this catalyst, a wide range of aromatic imines (including cyclic, acyclic, and heteroaromatic), alpha-iminoesters, and alpha,beta-unsaturated imines are reduced with good to excellent enantioselectivities.

Entities: Chemical

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Year: 2005 PMID： 16144373 DOI： 10.1021/ja050831a

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

9 in total

1. Re(V) and Re(III) complexes with sal2phen and triphenylphosphine: rearrangement, oxidation and reduction.

Authors: Stephanie Renee Lane; Nebiat Sisay; Brett Carney; Shorouk Dannoon; Stephen Williams; Hendrik Petrus Engelbrecht; Charles Leslie Barnes; Silvia Sabine Jurisson
Journal: Dalton Trans Date: 2010-11-15 Impact factor: 4.390

2. Enantioselective reduction of ketones and imines catalyzed by (CN-box)Re(V)-oxo complexes.

Authors: Kristine A Nolin; Richard W Ahn; Yusuke Kobayashi; Joshua J Kennedy-Smith; F Dean Toste
Journal: Chemistry Date: 2010-08-16 Impact factor: 5.236

3. Hydrosilation of Carbonyl-Containing Substrates Catalyzed by an Electrophilic η-Silane Iridium(III) Complex.

Authors: Sehoon Park; Maurice Brookhart
Journal: Organometallics Date: 2010-10 Impact factor: 3.876

4. Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8adihydro-8H-indeno[1,2-d]oxazole).

Authors: Julie L Hofstra; Travis J DeLano; Sarah E Reisman
Journal: Organic Synth Date: 2020-08-20

Enantioselective reduction of imines catalyzed by a rhenium(V)-oxo complex.

1. Re(V) and Re(III) complexes with sal2phen and triphenylphosphine: rearrangement, oxidation and reduction.

2. Enantioselective reduction of ketones and imines catalyzed by (CN-box)Re(V)-oxo complexes.

3. Hydrosilation of Carbonyl-Containing Substrates Catalyzed by an Electrophilic η-Silane Iridium(III) Complex.

4. Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8adihydro-8H-indeno[1,2-d]oxazole).

5. Studies on the Bisoxazoline and (-)-Sparteine Mediated Enantioselective Addition of Organolithium Reagents to Imines.

6. Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis.

Review 7. Hydrosilylation Reactions Catalyzed by Rhenium.

8. Bifunctional catalysis: direct reductive amination of aliphatic ketones with an iridium-phosphate catalyst.

9. The reaction of rhenium nitrosyl with a sterically hindered NHC-carbene.