Literature DB >> 22734694

Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation.

T Patrick Montgomery1, Abbas Hassan, Boyoung Y Park, Michael J Krische.   

Abstract

Upon exposure of acrylic ester 1 to alcohols 2a-i in the presence of a cyclometalated iridium catalyst modified by (-)-TMBTP, catalytic C-C coupling occurs, providing enantiomerically enriched 5-substituted α-exo-methylene γ-butyrolactones 3a-i. Bromination of the methylene butyrolactone products followed by zinc-mediated reductive aldehyde addition provides the disubstituted α-exo-methylene γ-butyrolactones 6a and 6b with good to excellent levels of diastereoselectivity.

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Year:  2012        PMID： 22734694      PMCID： PMC3397400          DOI： 10.1021/ja303839h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  19 in total

1.  2,2',5,5'-tetramethyl-4,4'-bis(diphenylphoshino)-3,3'-bithiophene: a new, very efficient, easily accessible, chiral biheteroaromatic ligand for homogeneous stereoselective catalysis

Authors: 
Journal:  J Org Chem       Date:  2000-04-07       Impact factor: 4.354

2.  Brønsted acid-catalyzed allylboration: short and stereodivergent synthesis of all four eupomatilone diastereomers with crystallographic assignments.

Authors:  Siu Hong Yu; Michael J Ferguson; Robert McDonald; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2005-09-21       Impact factor: 15.419

3.  Control of stereochemistry: a general synthesis of cis- or trans-beta,gamma-disubstituted-gamma-butyrolactones following Z-crotylboration.

Authors:  P Veeraraghavan Ramachandran; Debarshi Pratihar; Debanjan Biswas
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

4.  Acidity-directed synthesis of substituted gamma-butyrolactones from aliphatic aldehydes.

Authors:  P Veeraraghavan Ramachandran; Debarshi Pratihar
Journal:  Org Lett       Date:  2007-05-01       Impact factor: 6.005

Review 5.  The renaissance of alpha-methylene-gamma-butyrolactones: new synthetic approaches.

Authors:  Russell R A Kitson; Alessia Millemaggi; Richard J K Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Novel isomerically pure tetrasubstituted allylboronates: stereocontrolled synthesis of alpha-exomethylene gamma-lactones as aldol-like adducts with a stereogenic quaternary carbon center.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2002-02-13       Impact factor: 15.419

7.  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

8.  Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2002-10-02       Impact factor: 15.419

9.  Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry.

Authors:  Tim G Elford; Yuichiro Arimura; Siu Hong Yu; Dennis G Hall
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

10.  Total synthesis of the eupomatilones.

Authors:  Soumya Mitra; Srinivas Reddy Gurrala; Robert S Coleman
Journal:  J Org Chem       Date:  2007-10-11       Impact factor: 4.354
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  9 in total

1.  C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Authors:  Tao Liang; Sang Kook Woo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

2.  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

3.  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 4.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

Review 5.  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

6.  Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ-butyrolactones.

Authors:  Emma L McInturff; Jeffrey Mowat; Andrew R Waldeck; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-11-05       Impact factor: 15.419

7.  Asymmetric Synthesis of β-Substituted α-Methylenebutyro- lactones via TRIP-Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)-(-)-Hydroxymatairesinol.

Authors:  Michael Fuchs; Markus Schober; Andreas Orthaber; Kurt Faber
Journal:  Adv Synth Catal       Date:  2013-08-29       Impact factor: 5.837

8.  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

Review 9.  A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones.

Authors:  Joonseong Hur; Jaebong Jang; Jaehoon Sim
Journal:  Int J Mol Sci       Date:  2021-03-09       Impact factor: 5.923
  9 in total

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