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Literature DB >> 20459077

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

Jason R Zbieg¹, Emma L McInturff, Michael J Krische.

Abstract

Exposure of alcohols to allenamides in the presence of RuHCl(CO)(PPh(3))(3) and dippf [dippf = bis(diisopropylphosphino)ferrocene] results in hydrogen transfer to generate aldehyde-allylruthenium pairs, which engage in C-C coupling to form products of carbonyl aminoallylation as single anti-diastereomers.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2010 PMID： 20459077 PMCID： PMC2881554 DOI： 10.1021/ol1007235

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

27 in total

1. Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors: Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal: Aldrichimica Acta Date: 2008 Impact factor: 3.667

2. Some typical advances in the synthetic applications of allenes.

Authors: Shengming Ma
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

3. Hydrogen-mediated C-C bond formation: a broad new concept in catalytic C-C coupling.

Authors: Ming-Yu Ngai; Jong-Rock Kong; Michael J Krische
Journal: J Org Chem Date: 2007-02-16 Impact factor: 4.354

Review 4. Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.

Authors: Graham E Dobereiner; Robert H Crabtree
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

5. Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

Authors: Gabriela Guillena; Diego J Ramón; Miguel Yus
Journal: Chem Rev Date: 2010-03-10 Impact factor: 60.622

6. Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.

Authors: Ryan L Patman; Mani Raj Chaulagain; Vanessa M Williams; Michael J Krische
Journal: J Am Chem Soc Date: 2009-02-18 Impact factor: 15.419

7. Protecting-group-free synthesis of 3-tert-prenylated oxindoles: contiguous all-carbon quaternary centers via tertiary neopentyl substitution.

Authors: Christopher D Grant; Michael J Krische
Journal: Org Lett Date: 2009-10-15 Impact factor: 6.005

8. CO assistance in ligand exchange of a ruthenium racemization catalyst: identification of an acyl intermediate.

Authors: Jenny B Aberg; Jonas Nyhlén; Belén Martín-Matute; Timofei Privalov; Jan-E Bäckvall
Journal: J Am Chem Soc Date: 2009-07-15 Impact factor: 15.419

9. Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.

Authors: Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal: J Am Chem Soc Date: 2008-04-29 Impact factor: 15.419

10. Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Authors: Yu Lu; Michael J Krische
Journal: Org Lett Date: 2009-07-16 Impact factor: 6.005

27 in total

1. Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.

Authors: Joyce C Leung; Ryan L Patman; Brannon Sam; Michael J Krische
Journal: Chemistry Date: 2011-09-27 Impact factor: 5.236

2. Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors: Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal: Org Lett Date: 2010-11-19 Impact factor: 6.005

3. Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.

Authors: Kim Spielmann; Ming Xiang; Leyah A Schwartz; Michael J Krische
Journal: J Am Chem Soc Date: 2019-08-29 Impact factor: 15.419

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

Authors: Seung Wook Kim; Cole C Meyer; Binh Khanh Mai; Peng Liu; Michael J Krische
Journal: ACS Catal Date: 2019-09-11 Impact factor: 13.084

5. Formation of C-C bonds via ruthenium-catalyzed transfer hydrogenation().

Authors: Joseph Moran; Michael J Krische
Journal: Pure Appl Chem Date: 2012-03-13 Impact factor: 2.453

6. Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

Authors: John B Feltenberger; Richard P Hsung
Journal: Org Lett Date: 2011-05-25 Impact factor: 6.005

7. Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.

Authors: Wandi Zhang; Weijie Chen; Hongde Xiao; Michael J Krische
Journal: Org Lett Date: 2017-08-29 Impact factor: 6.005

8. Ruthenium-catalyzed C-C coupling of fluorinated alcohols with allenes: dehydrogenation at the energetic limit of β-hydride elimination.

Authors: Brannon Sam; Tom Luong; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2015-03-10 Impact factor: 15.336

Review 9. Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors: Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal: Top Curr Chem (Cham) Date: 2016-05-30

10. A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors: Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2018-02-02 Impact factor: 15.419