Literature DB >> 22668200

Primary amine, thiourea-based dual catalysis motif for synthesis of stereogenic, all-carbon quaternary center-containing cycloalkanones.

Jun Yong Kang1, Rich G Carter.   

Abstract

The enantioselective synthesis of α,α-disubstituted cycloalkanones has been developed using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and ring sizes are tolerated under the reaction conditions. A possible catalytic cycle is presented to explain the reactivity.

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Year:  2012        PMID: 22668200     DOI: 10.1021/ol301272r

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


  7 in total

Review 1.  Direct Asymmetric Alkylation of Ketones: Still Unconquered.

Authors:  Rafael Cano; Armen Zakarian; Gerard P McGlacken
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

2.  Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

Authors:  Xiaoyu Yang; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-26       Impact factor: 15.419

3.  Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α-Quaternary Ketones.

Authors:  Eric J Alexy; Scott C Virgil; Michael D Bartberger; Brian M Stoltz
Journal:  Org Lett       Date:  2017-09-13       Impact factor: 6.005

4.  Asymmetric fluorination of α-branched cyclohexanones enabled by a combination of chiral anion phase-transfer catalysis and enamine catalysis using protected amino acids.

Authors:  Xiaoyu Yang; Robert J Phipps; F Dean Toste
Journal:  J Am Chem Soc       Date:  2014-03-31       Impact factor: 15.419

5.  Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid.

Authors:  Xiaoyu Yang; F Dean Toste
Journal:  Chem Sci       Date:  2016-01-19       Impact factor: 9.825

6.  Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides.

Authors:  Jiawen Wang; Faqian He; Xiaoyu Yang
Journal:  Nat Commun       Date:  2021-11-18       Impact factor: 14.919

Review 7.  (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers.

Authors:  Giorgos Koutoulogenis; Nikolaos Kaplaneris; Christoforos G Kokotos
Journal:  Beilstein J Org Chem       Date:  2016-03-10       Impact factor: 2.883

  7 in total

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