Literature DB >> 22273041

Chiral Brønsted acid catalyzed enantioselective propargylation of aldehydes with allenylboronate.

Leleti Rajender Reddy1.   

Abstract

A highly enantioselective chiral Brønsted acid catalyzed propargylation of aldehydes with allenylboronate is described. The reaction is shown to be practical and quite general with a broad substrate scope covering aryl, polyaryl, heteroaryl, α,β-unsaturated, and aliphatic aldehydes.

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Year:  2012        PMID： 22273041     DOI： 10.1021/ol300075n

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


  7 in total

1.  Catalytic, Enantioselective Synthesis of Allenyl Boronates.

Authors:  De-Wei Gao; Yiyang Xiao; Mingyu Liu; Zhen Liu; Malkanthi K Karunananda; Jason S Chen; Keary M Engle
Journal:  ACS Catal       Date:  2018-03-21       Impact factor: 13.084

2.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

3.  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

4.  Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.

Authors:  Andy S Tsai; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-13       Impact factor: 6.005

5.  Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.

Authors:  Brett R Ambler; Sang Kook Woo; Michael J Krische
Journal:  ChemCatChem       Date:  2018-08-07       Impact factor: 5.686

6.  Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.

Authors:  Jian Zhao; Sybrand J T Jonker; Denise N Meyer; Göran Schulz; C Duc Tran; Lars Eriksson; Kálmán J Szabó
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

7.  Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation.

Authors:  Jucleiton J R Freitas; Queila P S B Freitas; Silvia R C P Andrade; Juliano C R Freitas; Roberta A Oliveira; Paulo H Menezes
Journal:  Beilstein J Org Chem       Date:  2020-02-04       Impact factor: 2.883
  7 in total

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