Issue 32, 2015
From the journal:

Organic & Biomolecular Chemistry

Trapping of carbolithiation-derived tertiary benzylic α-lithio piperidines with carbon electrophiles: Controlling the formation of α-amino quaternary and vicinal stereocenters†

Timothy K. Beng,*a   Nathan Fox,a   Daniel P. Bassler,a   Amir Alwali,a   Kayla Sincavagea  and  Ann Wens V. Silairea  

* Corresponding authors

a Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA
E-mail: beng@susqu.edu

Abstract

The interception of carbolithiation-derived tertiary benzylic α-lithio piperidines with carbon electrophiles, under HMPA-mediated conditions, has led to the diastereoselective synthesis of vicinally functionalized piperidines bearing α-amino quaternary stereocenters.

Graphical abstract: Trapping of carbolithiation-derived tertiary benzylic α-lithio piperidines with carbon electrophiles: Controlling the formation of α-amino quaternary and vicinal stereocenters

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Article information

DOI
https://doi.org/10.1039/C5OB01371B
Article type
Communication
Submitted
06 Jul 2015
Accepted
17 Jul 2015
First published
24 Jul 2015

Org. Biomol. Chem., 2015,13, 8647-8651

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Trapping of carbolithiation-derived tertiary benzylic α-lithio piperidines with carbon electrophiles: Controlling the formation of α-amino quaternary and vicinal stereocenters

T. K. Beng, N. Fox, D. P. Bassler, A. Alwali, K. Sincavage and A. W. V. Silaire, Org. Biomol. Chem., 2015, 13, 8647 DOI: 10.1039/C5OB01371B

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