N-Tert-butyldimethylsilyl imines as intermediates for the synthesis of amines and ketones

Article abstract of DOI:10.1080/00397919808004967

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.

Full text of DOI:10.1080/00397919808004967

This article was downloaded by: [Illinois State University Milner Library]
On: 06 November 2012, At: 10:15
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number:
1072954 Registered office: Mortimer House, 37-41 Mortimer Street,
London W1T 3JH, UK
Synthetic Communications:
An International Journal
for Rapid Communication of
Synthetic Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
N-tert-Butyldimethylsilyl
Imines as Intermediates for
the Synthesis of Amines and
Ketones
Margarita Ortiz-Marciales a , Liz M. Tirado
a , Roberto Colón a , María L. Ufret a , Ruth
Figueroa a , Marisabel Lebrón a , Melvin DeJesús
a , Johanna Martínez a & Tania Malavé a
a Department of Chemistry, University of Puerto
Rico Humacao, CUH Station, 00791, Puerto Rico
Version of record first published: 16 Aug 2006.
To cite this article: Margarita Ortiz-Marciales, Liz M. Tirado, Roberto Colón,
María L. Ufret, Ruth Figueroa, Marisabel Lebrón, Melvin DeJesús, Johanna
Martínez & Tania Malavé (1998): N-tert-Butyldimethylsilyl Imines as Intermediates
for the Synthesis of Amines and Ketones, Synthetic Communications: An
International Journal for Rapid Communication of Synthetic Organic Chemistry,
28:21, 4067-4075
To link to this article: http://dx.doi.org/10.1080/00397919808004967
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/
terms-and-conditions

This article may be used for research, teaching, and private study
purposes. Any substantial or systematic reproduction, redistribution,
reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden.
The publisher does not give any warranty express or implied or make
any representation that the contents will be complete or accurate or
up to date. The accuracy of any instructions, formulae, and drug doses
should be independently verified with primary sources. The publisher
shall not be liable for any loss, actions, claims, proceedings, demand, or
costs or damages whatsoever or howsoever caused arising directly or
indirectly in connection with or arising out of the use of this material.