Literature DB >> 19072064

Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles.

Laura L Anderson1, K A Woerpel.   

Abstract

The copper-catalyzed insertions of nitriles into the Si-C bonds of silacyclopropenes provide azasilacyclopentadienes, which can be converted to allylic amines after reduction and protodesilylation. The enamine functionality of azasilacyclopentadienes also participates in 1,4-addition reactions and undergoes a hydroboration and oxidation sequence to form an allylic 1,2-amino alcohol.

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Year:  2009        PMID： 19072064      PMCID： PMC2659660          DOI： 10.1021/ol802412b

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


  11 in total

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3.  Allylic amines via iridium-catalyzed C-C bond forming hydrogenation: imine vinylation in the absence of stoichiometric byproducts or metallic reagents.

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4.  Iridium-catalyzed, asymmetric amination of allylic alcohols activated by Lewis acids.

Authors:  Yasuhiro Yamashita; Apsara Gopalarathnam; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-05-25       Impact factor: 15.419

5.  Metal-catalyzed silylene transfer to imines: synthesis and reactivity of silaaziridines.

Authors:  Zulimar Nevárez; K A Woerpel
Journal:  Org Lett       Date:  2007-08-22       Impact factor: 6.005

6.  Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex.

Authors:  Robert E Kinder; Zhibin Zhang; Ross A Widenhoefer
Journal:  Org Lett       Date:  2008-06-21       Impact factor: 6.005

7.  Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Authors:  Carolyn E Anderson; Larry E Overman
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

8.  Dimethylzinc-mediated additions of alkenylzirconocenes to aldimines. New methodologies for allylic amine and C-cyclopropylalkylamine syntheses.

Authors:  Peter Wipf; Christopher Kendall; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2003-01-22       Impact factor: 15.419

9.  Scope and mechanism of formal S(N)2' substitution reactions of a monomeric imidozirconium complex with allylic electrophiles.

Authors:  Gojko Lalic; Jamin L Krinsky; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2008-03-08       Impact factor: 15.419

10.  Formation and utility of oxasilacyclopentenes derived from functionalized alkynes.

Authors:  Timothy B Clark; K A Woerpel
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419
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2.  The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

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  2 in total

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