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(2-Methoxyphenyl)dimethylsilyl Lithium and Cuprate Reagents Offer Unique Advantages in Multistep Synthesis†
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Abstract
The new silyllithium reagent 1 and the corresponding cyanocuprate 3 are readily generated under optimal conditions and are useful for the formation of C−Si bonds. Tamao−Fleming oxidation of such C−Si bonds can be effected under very mild conditions.
Citing Articles
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
Reductive Lithiation of Methyl Substituted Diarylmethylsilanes: Application to Silanediol Peptide Precursors
Dácil Hernández, Rasmus Mose, and Troels SkrydstrupOrganic Letters2011 13 (4), 732-735Reductive Lithiation of Methyl Substituted Diarylmethylsilanes: Application to Silanediol Peptide Precursors
Dácil Hernández, Rasmus Mose, and Troels SkrydstrupOrganic Letters2011 13 (4), 732-735Reductive lithiation of methyl-substituted diarylmethylsilanes using lithium naphthalenide represents a practical method for the preparation of the corresponding silyl lithium reagents. Their addition to chiral sulfinimines affords versatile precursors to ...
On the [3 + 2] Annulation of Cyclic Allylsilanes with N-Phenyltriazolinedione: An Enantio- and Diastereoselective Synthesis of cis-1,3-Diaminocyclitols
Raudra T. Dey and Tarun K. SarkarThe Journal of Organic Chemistry2010 75 (13), 4521-4529On the [3 + 2] Annulation of Cyclic Allylsilanes with N-Phenyltriazolinedione: An Enantio- and Diastereoselective Synthesis of cis-1,3-Diaminocyclitols
Raudra T. Dey and Tarun K. SarkarThe Journal of Organic Chemistry2010 75 (13), 4521-4529Improved conditions were found to trigger [3 + 2] annulation of cyclic allylsilanes with N-phenyltriazolinedione (PTAD); the products from this reaction were readily tailored into cis-1,3-diaminocyclitols in highly enantioenriched form with full ...
Building Functionalized Peptidomimetics: Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides
Haizhou Sun, Connor Martin, David Kesselring, Rebecca Keller, and Kevin D. MoellerJournal of the American Chemical Society2006 128 (42), 13761-13771Building Functionalized Peptidomimetics: Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides
Haizhou Sun, Connor Martin, David Kesselring, Rebecca Keller, and Kevin D. MoellerJournal of the American Chemical Society2006 128 (42), 13761-13771A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-...
Remote Substituent Effects upon the Rearrangements of Housane Cation Radicals
James B. Gerken, Selina C. Wang, Alejandro B. Preciado, Young Sam Park, Gisele Nishiguchi, Dean J. Tantillo, and R. Daniel LittleThe Journal of Organic Chemistry2005 70 (12), 4598-4608Remote Substituent Effects upon the Rearrangements of Housane Cation Radicals
James B. Gerken, Selina C. Wang, Alejandro B. Preciado, Young Sam Park, Gisele Nishiguchi, Dean J. Tantillo, and R. Daniel LittleThe Journal of Organic Chemistry2005 70 (12), 4598-4608The rearrangement of a series of housane-derived cation radicals was investigated. Surprisingly, 2-aryl-substituted systems rearranged regioselectively and in a process whose selectivity proved to be independent of the electronic character of para ...
Conjugate Additions of a Simple Monosilylcopper Reagent with Use of the CuI·DMS Complex: Stereoselectivities and a Dramatic Impact by DMS
Jesse Dambacher and Mikael BergdahlThe Journal of Organic Chemistry2005 70 (2), 580-589Conjugate Additions of a Simple Monosilylcopper Reagent with Use of the CuI·DMS Complex: Stereoselectivities and a Dramatic Impact by DMS
Jesse Dambacher and Mikael BergdahlThe Journal of Organic Chemistry2005 70 (2), 580-589Conjugate additions utilizing the simple monosilylcuprate reagent Li[PhMe2SiCuI] to α,β-unsaturated carbonyl compounds are described. The presence of dimethyl sulfide (DMS), either as a component originating from the (CuI)4(DMS)3 complex or as a solvent ...
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History
- Published In Issue October 18, 2001
- Received August 14, 2001
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