Literature DB >> 23231774

Iridium-catalyzed allylation of chiral β-stereogenic alcohols: bypassing discrete formation of epimerizable aldehydes.

Daniel C Schmitt1, Anne-Marie R Dechert-Schmitt, Michael J Krische.   

Abstract

The cyclometalated π-allyliridium 3,4-dinitro-C,O-benzoate complex modified by (R)- or (S)-Cl,MeO-BIPHEP promotes the transfer hydrogenative coupling of allyl acetate to β-stereogenic alcohols with good to excellent levels of catalyst-directed diastereoselectivity to furnish homoallylic alcohols. Remote electronic effects of the C,O-benzoate of the catalyst play a critical role in suppressing epimerization of the transient α-stereogenic aldehyde.

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Year:  2012        PMID： 23231774      PMCID： PMC3529126          DOI： 10.1021/ol3030692

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


  39 in total

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2.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
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3.  Enantioselective catalytic allylation of carbonyl groups by umpolung of pi-allyl palladium complexes.

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4.  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

5.  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

6.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

7.  Chiral Brønsted acid-catalyzed allylboration of aldehydes.

Authors:  Pankaj Jain; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

8.  Catalytic enantioselective Nozaki-Hiyama allylation reaction with tethered bis(8-quinolinolato) (TBOx) chromium complex.

Authors:  Guoyao Xia; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

9.  Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations.

Authors:  Vivek Rauniyar; Huimin Zhai; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2008-06-07       Impact factor: 15.419

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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  24 in total

1.  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

2.  Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors:  Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

3.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-12-24       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.  Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination.

Authors:  Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

7.  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

Review 8.  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

Review 9.  Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal:  Nat Prod Rep       Date:  2014-02-11       Impact factor: 13.423

10.  Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.

Authors:  Inji Shin; Gang Wang; Michael J Krische
Journal:  Chemistry       Date:  2014-08-28       Impact factor: 5.236
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