N-tert-Butyldimethylsilyl Imines as Intermediates for the Synthesis of Amines and Ketones

Margarita Ortiz-Marciales Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

Liz M. Tirado Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

Roberto Colón Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

María L. Ufret Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

Ruth Figueroa Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

Marisabel Lebrón Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

Melvin DeJesús Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

Johanna Martínez Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

Tania Malavé Department of Chemistry, University of Puerto Rico Humacao, CUH Station, 00791, Puerto Rico

show all

Abstract

Grignard reagents add to benzonitrile at low temperature catalyzed by CuBr and TBSCl affording N-TBS ketimines, which were investigated as intermediaries for the synthesis of primary amines and ketones. N-silylimines were easily obtained by an organolithium addition to benzonitrile followed by a reaction with TBSCl in CH₂Cl₂. In situ reduction of these imines by BH₃ and 1,3,2-oxazaborolidines 1 or 2 as chiral templates afforded the corresponding amines with modest to good enantiomeric excess.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

N-tert-Butyldimethylsilyl Imines as Intermediates for the Synthesis of Amines and Ketones

Information for

Open access

Opportunities

Help and information

N-tert-Butyldimethylsilyl Imines as Intermediates for the Synthesis of Amines and Ketones

Abstract

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature