Stereochemical course of the reductive spiroannulations of N-Boc and N-benzyl 2-cyanopiperidines |
| |
Authors: | Scott A. Wolckenhauer |
| |
Affiliation: | Department of Chemistry, 516 Rowland Hall, University of California-Irvine, Irvine, CA 92697-2025, USA |
| |
Abstract: | The stereochemical outcome of spiroannulations of N-protected 2-lithiopiperidines (generated by lithium di-tert-butyl biphenylide (LiDBB) mediated reductive lithiation of 2-cyanopiperidines) was investigated using deuterium labeled side-chains containing phosphate leaving groups. High stereoselectivity was observed when benzyl (Bn) protected 2-cyanopiperidines were employed, while tert-butoxycarbonyl (Boc) protected 2-cyanopiperidines afforded lower selectivity. Models are proposed to rationalize the results of this study. |
| |
Keywords: | Lithiation Alkylation Electrophilic addition |
本文献已被 ScienceDirect 等数据库收录! |
|