Literature DB >> 23206197

Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Yi Luan1, Scott E Schaus.   

Abstract

Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3'-Br(2)-BINOL. A two-step synthesis of (S)-4-methoxydalbergione in good yield and selectivity was achieved.

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Year:  2012        PMID： 23206197      PMCID： PMC4655814          DOI： 10.1021/ja309076g

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


  44 in total

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5.  Asymmetric conjugate alkenylation of enones catalyzed by chiral diols.

Authors:  T Robert Wu; J Michael Chong
Journal:  J Am Chem Soc       Date:  2007-04-03       Impact factor: 15.419

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Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

7.  Binaphthol-catalyzed asymmetric conjugate arylboration of enones.

Authors:  Heather M Turner; Jignesh Patel; Nootaree Niljianskul; J Michael Chong
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

8.  Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives.

Authors:  Tefsit Bekele; Meha H Shah; Jamison Wolfer; Ciby J Abraham; Anthony Weatherwax; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2006-02-15       Impact factor: 15.419

9.  Flavonoids from Dalbergia louvelii and their antiplasmodial activity.

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10.  Synthesis of 2H-chromenes and 1,2-dihydroquinolines from aryl aldehydes, amines, and alkenylboron compounds.

Authors:  Nicos A Petasis; Alexey Butkevich
Journal:  J Organomet Chem       Date:  2009-05-01       Impact factor: 2.369
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  17 in total

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Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

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Authors:  Javier Izquierdo; Ane Orue; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-07-11       Impact factor: 15.419

3.  Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes.

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Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419

4.  Multicomponent Condensation Reactions via ortho-Quinone Methides.

Authors:  Emily E Allen; Calvin Zhu; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

5.  Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

Authors:  Yao Jiang; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-04       Impact factor: 15.336

6.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors:  Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419

7.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

8.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

9.  Diastereoselective three-component synthesis of β-amino carbonyl compounds using diazo compounds, boranes, and acyl imines under catalyst-free conditions.

Authors:  Yi Luan; Jie Yu; Xiaowei Zhang; Scott E Schaus; Ge Wang
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10.  The domestication of ortho-quinone methides.

Authors:  Wen-Ju Bai; Jonathan G David; Zhen-Gao Feng; Marisa G Weaver; Kun-Liang Wu; Thomas R R Pettus
Journal:  Acc Chem Res       Date:  2014-12-03       Impact factor: 22.384
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