Literature DB >> 20387893

Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.

Jie Wu1, Yu Chen, James S Panek.   

Abstract

Enantioenriched homoallylic ethers containing a alpha,beta-unsaturated ester (syn-vinylogous aldol products) were directly accessed by Lewis acid catalyzed crotylation utilizing chiral silane 2. The reagents were prepared by enantioselective Si-H insertion to an alpha-diazovinylacetates using Davies' Rh(2)(DOSP)(4) catalyst or chiral Cu(I) Schiff base complex.

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Year:  2010        PMID： 20387893      PMCID： PMC3164278          DOI： 10.1021/ol100604m

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


  19 in total

1.  Total synthesis of (-)-dictyostatin.

Authors:  Gregory W O'Neil; Andrew J Phillips
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

2.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

3.  Catalytic enantioselective O-H insertion reactions.

Authors:  Thomas C Maier; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

4.  Copper-catalyzed asymmetric N-H insertion reactions: couplings of diazo compounds with carbamates to generate alpha-amino acids.

Authors:  Elaine C Lee; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2007-09-18       Impact factor: 15.419

5.  Copper-catalyzed highly enantioselective carbenoid insertion into Si-H bonds.

Authors:  Yong-Zhen Zhang; Shou-Fei Zhu; Li-Xin Wang; Qi-Lin Zhou
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions.

Authors:  J Hassfeld; M Christmann; M Kalesse
Journal:  Org Lett       Date:  2001-11-01       Impact factor: 6.005

7.  Palladium-catalyzed, one-pot, three-component synthesis of homoallylic amines from aldehydes, anisidine, and allyl trifluoroacetate.

Authors:  Robin E Grote; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

8.  Highly enantioselective insertion of carbenoids into O-H bonds of phenols: an efficient approach to chiral alpha-aryloxycarboxylic esters.

Authors:  Chao Chen; Shou-Fei Zhu; Bin Liu; Li-Xin Wang; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

9.  Lewis base activation of Lewis acids. Vinylogous aldol reactions.

Authors:  Scott E Denmark; Gregory L Beutner
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419

10.  Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper complexes of chiral spiro bisoxazolines.

Authors:  Bin Liu; Shou-Fei Zhu; Wei Zhang; Chao Chen; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-04-12       Impact factor: 15.419
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  4 in total

1.  Combined C-H functionalization/Cope rearrangement with vinyl ethers as a surrogate for the vinylogous Mukaiyama aldol reaction.

Authors:  Yajing Lian; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-07-18       Impact factor: 15.419

2.  Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling.

Authors:  Julie L Hofstra; Alan H Cherney; Ciara M Ordner; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-12-20       Impact factor: 15.419

3.  Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-03-16       Impact factor: 6.005

4.  Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage.

Authors:  Chenhui Chen; Hongliang Wang; Yufeng Sun; Jiayan Cui; Jianbo Xie; Yang Shi; Shijia Yu; Xin Hong; Zhan Lu
Journal:  iScience       Date:  2020-03-17
  4 in total

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