A One-Pot Formal [4 + 2] Cycloaddition Approach to Substituted Piperidines, Indolizidines, and Quinolizidines. Total Synthesis of Indolizidine (−)-209I

Heating a mixture of substituted N-benzyl γ-chloropropylamines, conjugated alkynoates or alkynones, sodium carbonate, and a catalytic amount of sodium iodide in i-PrOH at 70−83 °C delivers substituted piperidines in good yields. This transformation goes through a cascade Michael addition/alkylation...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-09, Vol.70 (18), p.7364-7370
Main Authors: Yu, Shanghai, Zhu, Wei, Ma, Dawei
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indolizines - chemical synthesis
Organic chemistry
Preparations and properties
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Summary:Heating a mixture of substituted N-benzyl γ-chloropropylamines, conjugated alkynoates or alkynones, sodium carbonate, and a catalytic amount of sodium iodide in i-PrOH at 70−83 °C delivers substituted piperidines in good yields. This transformation goes through a cascade Michael addition/alkylation process and represents a facile one-pot formal [4 + 2] cycloaddition approach to piperidine ring. Using secondary cyclic γ-chloropropylamines as substrates, this process produces substituted indolizidines or quinolizidines. On the basis of this approach, indolizidine (−)-209I is elaborated in 11 steps from methyl 2-hexenoate.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051080y