Stereochemical course of the reductive spiroannulations of N-Boc and N-benzyl 2-cyanopiperidines

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 stereoselecti...

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Published inTetrahedron Vol. 61; no. 13; pp. 3371 - 3381
Main Authors Wolckenhauer, Scott A., Rychnovsky, Scott D.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.03.2005
Elsevier
Subjects
Alkylation
Chemistry
Chemistry, Organic
Electrophilic addition
Lithiation
Physical Sciences
Science & Technology
Lithiation
Alkylation
Electrophilic addition
AMINONITRILES
LITHIOAMINE SYNTHETIC EQUIVALENTS
DISSOLVING METAL CONDITIONS
INTRAMOLECULAR CARBOLITHIATION
electrophilic addition
ALKYLLITHIUM
alkylation
ALPHA-AMINOORGANOLITHIUMS
lithiation
ANIONIC CYCLIZATIONS
PIPERIDINES
DIASTEREOISOMERS
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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. Graphical Abstract
AbstractList 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. (c) 2005 Elsevier Ltd. All rights reserved.
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. Graphical Abstract
Author Wolckenhauer, Scott A.
Rychnovsky, Scott D.
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Issue 13
Keywords Lithiation
Alkylation
Electrophilic addition
AMINONITRILES
LITHIOAMINE SYNTHETIC EQUIVALENTS
DISSOLVING METAL CONDITIONS
INTRAMOLECULAR CARBOLITHIATION
electrophilic addition
ALKYLLITHIUM
alkylation
ALPHA-AMINOORGANOLITHIUMS
lithiation
ANIONIC CYCLIZATIONS
PIPERIDINES
DIASTEREOISOMERS
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Snippet The stereochemical outcome of spiroannulations of N-protected 2-lithiopiperidines (generated by lithium di- tert-butyl biphenylide (LiDBB) mediated reductive...
The stereochemical outcome of spiroannulations of N-protected 2-lithiopiperidines (generated by lithium di-tert-butyl biphenylide (LiDBB) mediated reductive...
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SubjectTerms Alkylation
Chemistry
Chemistry, Organic
Electrophilic addition
Lithiation
Physical Sciences
Science & Technology
Title Stereochemical course of the reductive spiroannulations of N-Boc and N-benzyl 2-cyanopiperidines
URI https://dx.doi.org/10.1016/j.tet.2005.01.099
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