Literature DB >> 21829853

Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability.

Abbas Hassan1, Ian A Townsend, Michael J Krische.   

Abstract

Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki-Hiyama methallylations from the alcohol or aldehyde oxidation level via iridium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetate does not react efficiently. Double methallylation of 1,3-propanediol provides the C(2)-symmetric adduct as a single enantiomer, as determined by HPLC analysis.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21829853      PMCID： PMC3225001          DOI： 10.1039/c1cc14392a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  32 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.  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

3.  Enhanced anti-diastereo- and enantioselectivity in alcohol-mediated carbonyl crotylation using an isolable single component iridium catalyst.

Authors:  Xin Gao; Ian A Townsend; Michael J Krische
Journal:  J Org Chem       Date:  2011-03-04       Impact factor: 4.354

4.  Catalytic asymmetric methallylation of ketones with an (H8-BINOLate)Ti-based catalyst.

Authors:  Jeung Gon Kim; Elizabeth H Camp; Patrick J Walsh
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

5.  "Inverse-electron-demand" ligand substitution: experimental and computational insights into olefin exchange at palladium(0).

Authors:  Brian V Popp; Joseph L Thorman; Christine M Morales; Clark R Landis; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2004-11-17       Impact factor: 15.419

6.  Dramatic improvement in catalyst loadings and molar ratios of coupling partners for Ni/Cr-mediated coupling reactions: heterobimetallic catalysts.

Authors:  Xiang Liu; James A Henderson; Takeo Sasaki; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

7.  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

8.  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

9.  Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.

Authors:  Hugo Lachance; Xiaosong Lu; Michel Gravel; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2003-08-27       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
View more
  12 in total

1.  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

2.  Consecutive iridium catalyzed C-C and C-H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C-H (2-fluoro)allylation of primary alcohols.

Authors:  Abbas Hassan; T Patrick Montgomery; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2012-04-04       Impact factor: 6.222

3.  Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes.

Authors:  James M Cabrera; Johannes Tauber; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-04       Impact factor: 15.336

4.  Nickel-Catalyzed Cross-Coupling of Vinyl Dioxanones to Form Enantiomerically Enriched Cyclopropanes.

Authors:  Yi-An Guo; Tao Liang; Seung Wook Kim; Hongde Xiao; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

5.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

6.  Direct, Mild, and General n-Bu4NBr-Catalyzed Aldehyde Allylsilylation with Allyl Chlorides.

Authors:  Makeda A Tekle-Smith; Kevin S Williamson; Isaac F Hughes; James L Leighton
Journal:  Org Lett       Date:  2017-11-03       Impact factor: 6.005

7.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384

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

9.  Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D.

Authors:  Gilmar A Brito; Woo-Ok Jung; Minjin Yoo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

10.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.