Literature DB >> 11101451

Enantiocontrolled synthesis of highly functionalized tropanes via [5 + 2] cycloaddition to eta(3)-pyridinylmolybdenum pi-complexes.

H C Malinakova1, L S Liebeskind.   

Abstract

[reaction: see text] A chiral, nonracemic eta(3)-pyridinyl scaffold participates in [5 + 2] cycloaddition with electron-deficient alkenes, an allene, and an alkyne to give eta(3)-allylmolybdenum bicyclic adducts. The adducts can be demetalated, providing a convergent route to highly functionalized tropanes. High enantiocontrol can be achieved throughout the cycloaddition and demetalation sequence.

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Year:  2000        PMID： 11101451     DOI： 10.1021/ol000288x

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


  8 in total

1.  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

2.  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

3.  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

4.  The enantiomeric scaffold approach to highly functionalized 1-oxadecalines: enantio- and regiocontrolled [4 + 2] cycloadditions of 5-alkenyl-eta3-pyranylmolybdenum complexes.

Authors:  Ramón Gómez Arrayás; Jingjun Yin; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2007-02-14       Impact factor: 15.419

5.  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

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

Authors:  Thomas C Coombs; Maurice D Lee; Heilam Wong; Matthew Armstrong; Bo Cheng; Wenyong Chen; Alessandro F Moretto; Lanny S Liebeskind
Journal:  J Org Chem       Date:  2008-01-03       Impact factor: 4.354

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
  8 in total

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