Literature DB >> 16417383

Enantioselective TADMAP-catalyzed carboxyl migration reactions for the synthesis of stereogenic quaternary carbon.

Scott A Shaw1, Pedro Aleman, Justin Christy, Jeff W Kampf, Porino Va, Edwin Vedejs.   

Abstract

The chiral, nucleophilic catalyst TADMAP [1, 3-(2,2,2-triphenyl-1-acetoxyethyl)-4-(dimethylamino)pyridine] has been prepared from 3-lithio-4-(dimethylamino)pyridine (5) and triphenylacetaldehyde (3), followed by acylation and resolution. TADMAP catalyzes the carboxyl migration of oxazolyl, furanyl, and benzofuranyl enol carbonates with good to excellent levels of enantioselection. The oxazole reactions are especially efficient and are used to prepare chiral lactams (23) and lactones (30) containing a quaternary asymmetric carbon. TADMAP-catalyzed carboxyl migrations in the indole series are relatively slow and proceed with inconsistent enantioselectivity. Modeling studies (B3LYP/6-31G*) have been used in qualitative correlations of catalyst conformation, reactivity, and enantioselectivity.

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Year:  2006        PMID： 16417383      PMCID： PMC2532525          DOI： 10.1021/ja056150x

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


  45 in total

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Authors:  Melissa M. Vasbinder; Elizabeth R. Jarvo; Scott J. Miller
Journal:  Angew Chem Int Ed Engl       Date:  2001-08-03       Impact factor: 15.336

3.  The second total synthesis of diazonamide A.

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Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

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Authors:  Alan C. Spivey; Steven J. Woodhead; Matthew Weston; Benjamin I. Andrews
Journal:  Angew Chem Int Ed Engl       Date:  2001-02-16       Impact factor: 15.336

5.  Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetals.

Authors:  Ara H Mermerian; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

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Journal:  J Am Chem Soc       Date:  2002-08-07       Impact factor: 15.419

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Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

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Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419
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  15 in total

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Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

2.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

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Authors:  Trisha A Duffey; James A Mackay; Edwin Vedejs
Journal:  J Org Chem       Date:  2010-07-16       Impact factor: 4.354

4.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

5.  Enantioselective total synthesis of (+)-gliocladine C: convergent construction of cyclotryptamine-fused polyoxopiperazines and a general approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors.

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Journal:  J Am Chem Soc       Date:  2011-04-07       Impact factor: 15.419

Review 6.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

7.  Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oximes.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2012-12-07       Impact factor: 6.222

8.  AcOLeDMAP and BnOLeDMAP: conformationally restricted nucleophilic catalysts for enantioselective rearrangement of indolyl acetates and carbonates.

Authors:  Trisha A Duffey; Scott A Shaw; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

9.  Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.

Authors:  Masaki Hayashi; Shoshana Bachman; Satoshi Hashimoto; Chad C Eichman; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-07-15       Impact factor: 15.419

10.  Selective syntheses of Δ(α,β) and Δ(β,γ) butenolides from allylic cyclopropenecarboxylates via tandem ring expansion/[3,3]-sigmatropic rearrangements.

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Journal:  Org Lett       Date:  2013-03-20       Impact factor: 6.005
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