Literature DB >> 31857913

Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.

Seung Wook Kim1, Cole C Meyer1, Binh Khanh Mai2, Peng Liu2, Michael J Krische1.   

Abstract

The use of gaseous allene as an allyl pronucleophile in enantioselective aldehyde reductive coupling is described. Notably, using the same antipode of chiral ligand, (S)-tol-BINAP, an inversion of enantioselectivity is observed for allene vs allyl acetate pronucleophiles. Experimental and computational studies corroborate intervention of diastereomeric π-allyliridium-C,O-benzoate complexes, which arise via allene hydrometalation (from a pentacoordinate iridium hydride) vs allyl acetate ionization (from a square planar iridium species).

Entities:  

Keywords:  allylation; enantioselective; iridium; reductive coupling; transfer hydrogenation

Year:  2019        PMID： 31857913      PMCID： PMC6921087          DOI： 10.1021/acscatal.9b03695

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  40 in total

1.  Iridium-catalyzed H/D exchange into organic compounds in water.

Authors:  Steven R Klei; Jeffrey T Golden; T Don Tilley; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

2.  Allenamide hydro-hydroxyalkylation: 1,2-amino alcohols via ruthenium-catalyzed carbonyl anti-aminoallylation.

Authors:  Jason R Zbieg; Emma L McInturff; Michael J Krische
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

3.  Catalytic C-C coupling via transfer hydrogenation: reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level.

Authors:  John F Bower; Eduardas Skucas; Ryan L Patman; Michael J Krische
Journal:  J Am Chem Soc       Date:  2007-11-17       Impact factor: 15.419

4.  Creation of quaternary stereocenters in carbonyl allylation reactions.

Authors:  Ilan Marek; Genia Sklute
Journal:  Chem Commun (Camb)       Date:  2006-12-06       Impact factor: 6.222

5.  Ruthenium catalyzed C-C bond formation via transfer hydrogenation: branch-selective reductive coupling of allenes to paraformaldehyde and higher aldehydes.

Authors:  Ming-Yu Ngai; Eduardas Skucas; Michael J Krische
Journal:  Org Lett       Date:  2008-06-06       Impact factor: 6.005

6.  Greening Organic Chemistry with Process Chemistry.

Authors:  Kai Rossen
Journal:  J Org Chem       Date:  2019-04-19       Impact factor: 4.354

7.  Origins of Enantioselectivity in Asymmetric Radical Additions to Octahedral Chiral-at-Rhodium Enolates: A Computational Study.

Authors:  Shuming Chen; Xiaoqiang Huang; Eric Meggers; K N Houk
Journal:  J Am Chem Soc       Date:  2017-11-29       Impact factor: 15.419

8.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level using allyl acetate as an allyl metal surrogate.

Authors:  In Su Kim; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

9.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition.

Authors:  In Su Kim; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

10.  Elongation of 1,3-polyols via iterative catalyst-directed carbonyl allylation from the alcohol oxidation level.

Authors:  Abbas Hassan; Yu Lu; Michael J Krische
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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  4 in total

1.  Kinetic, ESI-CID-MS and Computational Studies of π-Allyliridium C,O-Benzoate-Catalyzed Allylic Amination: Understanding the Effect of Cesium Ion.

Authors:  Woo-Ok Jung; Binh Khanh Mai; Minjin Yoo; Samuel W J Shields; Jason R Zbieg; Craig E Stivala; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2022-03-08       Impact factor: 13.700

2.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084

3.  Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines.

Authors:  Woo-Ok Jung; Binh Khanh Mai; Brian J Spinello; Zachary J Dubey; Seung Wook Kim; Craig E Stivala; Jason R Zbieg; Peng Liu; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-06-21       Impact factor: 16.383

Review 4.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020
  4 in total

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