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薄荷醇、8-甲基薄荷醇和8-苯基薄荷醇-2-烷基丙二酸酯的非对映选择性阳极杂偶联和自偶联反应

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates.

作者信息

Letzel Matthias C, Schäfer Hans J, Fröhlich Roland

机构信息

Organisch-Chemisches Institut der Westfälischen Wilhelms- Universität, Corrensstraße 40, D-48149 Münster, Germany.

出版信息

Beilstein J Org Chem. 2017 Jan 5;13:33-42. doi: 10.3762/bjoc.13.5. eCollection 2017.

DOI:10.3762/bjoc.13.5
PMID:28179946
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5238534/
Abstract

Diastereoselective radical coupling was achieved with chiral auxiliaries. The radicals were generated by anodic decarboxylation of five malonic acid derivatives. These were prepared from benzyl malonates and four menthol auxiliaries. Coelectrolyses with 3,3-dimethylbutanoic acid in methanol at platinum electrodes in an undivided cell afforded hetero-coupling products in 22-69% yield with a diastereoselectivity ranging from 5 to 65% de. Electrolyses without a coacid led to diastereomeric homo-coupling products in 21-50% yield with ratios of diastereomers being 1.17:2.00:0.81 to 7.03:2.00. The stereochemistry of the new stereogenic centers was confirmed by X-ray structure analysis and C NMR data.

摘要

通过手性助剂实现了非对映选择性自由基偶联。自由基由五种丙二酸衍生物的阳极脱羧反应产生。这些衍生物由苄基丙二酸酯和四种薄荷醇助剂制备而成。在未分隔的电池中，于铂电极上在甲醇中与3,3 - 二甲基丁酸进行共电解，得到的杂偶联产物产率为22 - 69%，非对映选择性范围为5至65%的对映体过量值（de）。没有共酸存在时的电解反应生成了非对映体的均偶联产物，产率为21 - 50%，非对映体比例为1.17:2.00:0.81至7.03:2.00。新立体中心的立体化学结构通过X射线结构分析和碳核磁共振（C NMR）数据得以证实。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/cd7a95e41075/Beilstein_J_Org_Chem-13-33-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/3db46da67de4/Beilstein_J_Org_Chem-13-33-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/eaea3de18599/Beilstein_J_Org_Chem-13-33-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/cdd667cace05/Beilstein_J_Org_Chem-13-33-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/4f4e5a90fa8c/Beilstein_J_Org_Chem-13-33-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/0d889eaccc7f/Beilstein_J_Org_Chem-13-33-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/843ae769bfb1/Beilstein_J_Org_Chem-13-33-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/4c296a23f3bd/Beilstein_J_Org_Chem-13-33-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/9662104c46fe/Beilstein_J_Org_Chem-13-33-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/4219a1d35586/Beilstein_J_Org_Chem-13-33-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/e86c36e7b1df/Beilstein_J_Org_Chem-13-33-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/cd7a95e41075/Beilstein_J_Org_Chem-13-33-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/3db46da67de4/Beilstein_J_Org_Chem-13-33-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/eaea3de18599/Beilstein_J_Org_Chem-13-33-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/cdd667cace05/Beilstein_J_Org_Chem-13-33-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/4f4e5a90fa8c/Beilstein_J_Org_Chem-13-33-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/0d889eaccc7f/Beilstein_J_Org_Chem-13-33-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/843ae769bfb1/Beilstein_J_Org_Chem-13-33-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/4c296a23f3bd/Beilstein_J_Org_Chem-13-33-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/9662104c46fe/Beilstein_J_Org_Chem-13-33-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/4219a1d35586/Beilstein_J_Org_Chem-13-33-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/e86c36e7b1df/Beilstein_J_Org_Chem-13-33-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cdf/5238534/cd7a95e41075/Beilstein_J_Org_Chem-13-33-g012.jpg

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