Literature DB >> 10880192

A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via suzuki-type coupling of acid chlorides with cyclopropylboronic acids.

H Chen1, M Z Deng.   

Abstract

[reaction: see text] The palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with acyl chlorides was achieved by the combination of Ag(2)O and K(2)CO(3) as the base. Highly enantiomerically enriched cyclopropyl ketones (ee >90%) were also obtained by the reaction of corresponding chiral cyclopropylboronic acids.

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Year:  2000        PMID: 10880192     DOI: 10.1021/ol000013h

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


  6 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

Authors:  Xinghua Ma; Benjamin Murray; Mark R Biscoe
Journal:  Nat Rev Chem       Date:  2020-09-24       Impact factor: 34.035

3.  Enantioselective homocrotylboration of aliphatic aldehydes.

Authors:  Hongkun Lin; Wenbo Pei; Hao Wang; Kendall N Houk; Isaac J Krauss
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

4.  A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.

Authors:  David M Knapp; Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

5.  Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki-Miyaura reactions: relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation.

Authors:  Vadim V Bardin; Anton Yu Shabalin; Nicolay Yu Adonin
Journal:  Beilstein J Org Chem       Date:  2015-05-04       Impact factor: 2.883

6.  Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones.

Authors:  Javad Amani; Esmat Sodagar; Gary A Molander
Journal:  Org Lett       Date:  2016-02-01       Impact factor: 6.005

  6 in total

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