Literature DB >> 18171075

Practical, scalable, high-throughput approaches to eta3-pyranyl and eta3-pyridinyl organometallic enantiomeric scaffolds using the Achmatowicz reaction.

Thomas C Coombs1, Maurice D Lee, Heilam Wong, Matthew Armstrong, Bo Cheng, Wenyong Chen, Alessandro F Moretto, Lanny S Liebeskind.   

Abstract

A unified strategy for the high-throughput synthesis of multigram quantities of the eta(3)-oxopyranyl- and eta(3)-oxopyridinylmolybdenum complexes TpMo(CO)(2)(eta(3)-oxopyranyl) and TpMo(CO)(2)(eta(3)-oxopyridinyl) is described (Tp = hydridotrispyrazolylborato). The strategy uses the oxa- and aza-Achmatowicz reaction for the preparation of these organometallic enantiomeric scaffolds, in both racemic and high enantiopurity versions.

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Year:  2008        PMID: 18171075      PMCID: PMC2652699          DOI: 10.1021/jo702006z

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  36 in total

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Authors:  R G Arrayás; L S Liebeskind
Journal:  J Am Chem Soc       Date:  2001-06-27       Impact factor: 15.419

2.  Synthesis of Heterocyclic and Carbocyclic Compounds via Alkynyl, Allyl, and Propargyl Organometallics of Cyclopentadienyl Iron, Molybdenum, and Tungsten Complexes.

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Review 3.  Origins, current status, and future challenges of green chemistry.

Authors:  Paul T Anastas; Mary M Kirchhoff
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Review 4.  Asymmetric organocatalysis.

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Journal:  Org Biomol Chem       Date:  2005-02-09       Impact factor: 3.876

5.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
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6.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

7.  Chiral oxazolopiperidone lactams: versatile intermediates for the enantioselective synthesis of piperidine-containing natural products.

Authors:  Carmen Escolano; Mercedes Amat; Joan Bosch
Journal:  Chemistry       Date:  2006-11-06       Impact factor: 5.236

8.  Diastereoselective conjugate additions to pi-allylmolybdenum complexes: a stereocontrolled route to 3,4,5-trisubstituted gamma-butyrolactones.

Authors:  Anthony J Pearson; Eugen F Mesaros
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

9.  Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam.

Authors:  Mercedes Amat; Núria Llor; José Hidalgo; Carmen Escolano; Joan Bosch
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354

10.  Enantioselective synthesis of cis- and trans-3,5-disubstituted piperidines. Synthesis of 20S- and 20R-dihydrocleavamine.

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Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

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  9 in total

1.  Toward the synthesis of (+)-peloruside A via an intramolecular vinylogous aldol reaction.

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2.  Organometallic enantiomeric scaffolding: a strategy for the enantiocontrolled construction of regio- and stereodivergent trisubstituted piperidines from a common precursor.

Authors:  Heilam Wong; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

3.  Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  RSC Adv       Date:  2016-11-24       Impact factor: 3.361

4.  Novel Substitutions of 1-Alkoxy- and 1-Arylsulfonyloxy-η-Allylmolybdenum Complexes. A Case for η-Alkenyl Carbene Complexes as Intermediates.

Authors:  Thomas C Coombs; Wenwei Huang; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  Organometallics       Date:  2010-11-08       Impact factor: 3.876

5.  Organometallic enantiomeric scaffolding. A molybdenum-mediated intramolecular nucleophilic ketalization-demetalation cascade. Total synthesis of (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brevicomin.

Authors:  Bo Cheng; Lanny S Liebeskind
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

6.  Organometallic enantiomeric scaffolding: general access to 2-substituted oxa- and azabicyclo[3.2.1]octenes via a Brønsted acid catalyzed [5 + 2] cycloaddition reaction.

Authors:  Ethel C Garnier; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2008-05-15       Impact factor: 15.419

7.  Organometallic enantiomeric scaffolding. Sequential semipinacol/1,5-"Michael-like" reactions as a strategic approach to bridgehead-quaternary center aza[3.3.1]bicyclics: application to the total synthesis of (-)-adaline.

Authors:  Thomas C Coombs; Yongqiang Zhang; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

8.  A new reaction motif: "homo-S(N)2'-like" direct nucleophilic addition to neutral eta(3)-allylmolybdenum complexes. total synthesis of the antimalarial (+)-isofebrifugine.

Authors:  Wenyong Chen; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419

Review 9.  Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine.

Authors:  Dimas J P Lima; Antonio E G Santana; Michael A Birkett; Ricardo S Porto
Journal:  Beilstein J Org Chem       Date:  2021-01-05       Impact factor: 2.883

  9 in total

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