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立体选择性的硝基曼尼希/内酰胺化级联反应用于 5-硝基哌啶-2-酮及相关杂环的直接合成。

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles.

机构信息

The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.

出版信息

Beilstein J Org Chem. 2012;8:567-78. doi: 10.3762/bjoc.8.64. Epub 2012 Apr 16.

DOI:10.3762/bjoc.8.64
PMID:22563355
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3343283/
Abstract

A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation of the heterocycles was used to install contiguous and fully substituted stereocentres in the synthesis of substituted piperidines.

摘要

一种多功能的硝基-Mannich/内酰胺化级联反应已被开发用于直接立体选择性合成重修饰的 5-硝基哌啶-2-酮和相关杂环化合物。通过将对映选择性的有机催化迈克尔加成与非对映选择性的硝基-Mannich/内酰胺化级联反应相结合，在一锅四组分反应中合成了高对映体过量的取代的 5-硝基哌啶-2-酮。对杂环化合物进行原脱硝化和化学选择性还原操作，可在取代哌啶的合成中引入连续的和完全取代的立体中心。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/aa56334c513d/Beilstein_J_Org_Chem-08-567-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/9b355801c918/Beilstein_J_Org_Chem-08-567-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/c420604952f2/Beilstein_J_Org_Chem-08-567-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/040562709a2d/Beilstein_J_Org_Chem-08-567-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/83f84db97182/Beilstein_J_Org_Chem-08-567-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/bd5943b60962/Beilstein_J_Org_Chem-08-567-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/491c04919ef2/Beilstein_J_Org_Chem-08-567-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/e6296f98d5b8/Beilstein_J_Org_Chem-08-567-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/18a575304417/Beilstein_J_Org_Chem-08-567-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/5172e4ca2cb5/Beilstein_J_Org_Chem-08-567-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/f61480ce766d/Beilstein_J_Org_Chem-08-567-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/cb8a2c0008f3/Beilstein_J_Org_Chem-08-567-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/6d15afc7136b/Beilstein_J_Org_Chem-08-567-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/aa56334c513d/Beilstein_J_Org_Chem-08-567-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/9b355801c918/Beilstein_J_Org_Chem-08-567-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/c420604952f2/Beilstein_J_Org_Chem-08-567-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/040562709a2d/Beilstein_J_Org_Chem-08-567-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/83f84db97182/Beilstein_J_Org_Chem-08-567-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/bd5943b60962/Beilstein_J_Org_Chem-08-567-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/491c04919ef2/Beilstein_J_Org_Chem-08-567-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/e6296f98d5b8/Beilstein_J_Org_Chem-08-567-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/18a575304417/Beilstein_J_Org_Chem-08-567-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/5172e4ca2cb5/Beilstein_J_Org_Chem-08-567-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/f61480ce766d/Beilstein_J_Org_Chem-08-567-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/cb8a2c0008f3/Beilstein_J_Org_Chem-08-567-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/6d15afc7136b/Beilstein_J_Org_Chem-08-567-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4401/3343283/aa56334c513d/Beilstein_J_Org_Chem-08-567-g014.jpg

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