Literature DB >> 34093103

Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Banruo Huang1, Ying He1, Mark D Levin1, Jaime A S Coelho1,2, Robert G Bergman1, F Dean Toste1.   

Abstract

A chiral phosphoric acid-catalyzed kinetic resolution and desymmetrization of para-quinols operating via oxa-Michael addition was developed and subsequently subjected to mechanistic study. Good to excellent s-factors/enantioselectivities were obtained over a broad range of substrates. Kinetic studies were performed, and DFT studies favor a hydrogen bonding activation mode. The mechanistic studies provide insights to previously reported chiral anion phase transfer reactions involving chiral phosphate catalysts in combination with boronic acids.

Entities:  

Keywords:  asymmetric catalysis; chiral phosphoric acid; directed reactivity; kinetics; oxa-Michael addition; reaction mechanisms

Year:  2019        PMID： 34093103      PMCID： PMC8174618          DOI： 10.1002/adsc.201900816

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  47 in total

1.  Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

Authors:  Aaron D Lackner; Andrew V Samant; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

2.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

3.  An enantioselective organocatalytic oxidative dearomatization strategy.

Authors:  Ngoc T Vo; Robert D M Pace; Fionn O'Hara; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

4.  On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

Authors:  David D Ford; Dan Lehnherr; C Rose Kennedy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

5.  Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts.

Authors:  Carolina M Avila; Jigar S Patel; Yernaidu Reddi; Masato Saito; Hosea M Nelson; Hunter P Shunatona; Matthew S Sigman; Raghavan B Sunoj; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-18       Impact factor: 15.336

6.  Enantioselective fluoroamination: 1,4-addition to conjugated dienes using anionic phase-transfer catalysis.

Authors:  Hunter P Shunatona; Natalja Früh; Yi-Ming Wang; Vivek Rauniyar; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-13       Impact factor: 15.336

7.  Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp3)-H Acetalization.

Authors:  Baihua Ye; Jie Zhao; Ke Zhao; Jeffrey M McKenna; F Dean Toste
Journal:  J Am Chem Soc       Date:  2018-06-25       Impact factor: 15.419

8.  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

9.  Enantioselective fluorination of homoallylic alcohols enabled by the tuning of non-covalent interactions.

Authors:  Jaime A S Coelho; Akira Matsumoto; Manuel Orlandi; Margaret J Hilton; Matthew S Sigman; F Dean Toste
Journal:  Chem Sci       Date:  2018-08-03       Impact factor: 9.825

10.  Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst.

Authors:  H M Nelson; J S Patel; H P Shunatona; F D Toste
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825
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