Literature DB >> 19586067

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

Abbas Hassan1, Yu Lu, Michael J Krische.   

Abstract

Iterative enantioselective carbonyl allylation from the alcohol oxidation level under the conditions of iridium catalyzed transfer hydrogenation enables chain elongation of 1,3-polyols. High levels of catalyst-directed enantioselectivity and diastereoselectivity are observed.

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Year:  2009        PMID： 19586067      PMCID： PMC2720825          DOI： 10.1021/ol901136w

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


  20 in total

1.  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

2.  Direct, catalytic hydroaminoalkylation of unactivated olefins with N-alkyl arylamines.

Authors:  Seth B Herzon; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-05-03       Impact factor: 15.419

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

4.  Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde.

Authors:  Gráinne C Hargaden; Timothy P O'Sullivan; Patrick J Guiry
Journal:  Org Biomol Chem       Date:  2007-12-20       Impact factor: 3.876

5.  Titanium-catalyzed hydroaminoalkylation of alkenes by C-H bond activation at sp3 centers in the alpha-position to a nitrogen atom.

Authors:  Raphael Kubiak; Insa Prochnow; Sven Doye
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Formation of C-C Bonds via Ruthenium Catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level.

Authors:  Fumitoshi Shibahara; Michael J Krische
Journal:  Chem Lett       Date:  2008       Impact factor: 1.389

7.  Selective C-H activation alpha to primary amines. Bridging metallaaziridines for catalytic, intramolecular alpha-alkylation.

Authors:  Jason A Bexrud; Patrick Eisenberger; David C Leitch; Philippa R Payne; Laurel L Schafer
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

8.  Recent advances in the activation of boron and silicon reagents for stereocontrolled allylation reactions.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-13       Impact factor: 15.336

9.  1,n-glycols as dialdehyde equivalents in iridium-catalyzed enantioselective carbonyl allylation and iterative two-directional assembly of 1,3-polyols.

Authors:  Yu Lu; In Su Kim; Abbas Hassan; David J Del Valle; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexoses.

Authors:  Soo Bong Han; Jong Rock Kong; Michael J Krische
Journal:  Org Lett       Date:  2008-08-26       Impact factor: 6.005
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  33 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.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

3.  Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.

Authors:  Inji Shin; Suckchang Hong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

Review 4.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

5.  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

6.  Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins.

Authors:  Paul E Gormisky; M Christina White
Journal:  J Am Chem Soc       Date:  2011-07-27       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.  Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

Authors:  Takahiko Itoh; T Patrick Montgomery; Antonio Recio; Michael J Krische
Journal:  Org Lett       Date:  2014-01-14       Impact factor: 6.005

9.  Diastereo- and enantioselective anti-alkoxyallylation employing allylic gem-dicarboxylates as allyl donors via iridium-catalyzed transfer hydrogenation.

Authors:  Soo Bong Han; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

Review 10.  Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors:  John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-23       Impact factor: 15.336
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