Selenium Dioxide Promoted α-Keto N-Acylation of Sulfoximines Under Mild Reaction Conditions

被引：8

作者：

Baranwal, Siddharth ^{[1
]}

Gupta, Surabhi ^{[1
]}

Kandasamy, Jeyakumar ^{[1
]}

机构：

[1] Indian Inst Technol BHU, Dept Chem, Varanasi 221005, Uttar Pradesh, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 07期

关键词：

alpha-Keto N-acyl sulfoximine; Aryl methyl ketones; Aryl acetaldehyde; Arylacetylene; Selenium oxide; AROYLATION; KETOAMIDE; DISCOVERY; ARYLATION; LIGANDS; CONVERSION;

D O I：

10.1002/ajoc.202100298

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method for the synthesis of alpha-ketoamides of sulfoximines was developed from NH-sulfoximines and acetophenones using selenium dioxide as an oxidant. The reactions proceeded under mild conditions in the absence of any additives and provided good to excellent yields of alpha-keto-N-acylsulfoximines. Moreover, the optimized condition was well-suited to the task of alpha-ketoacylation of sulfoximines with phenylacetaldehyde and arylacetylenes. alpha-Hydroxy N-acylsulfoximines were obtained in good yields from alpha-keto N-acylsulfoximines via reduction or Grignard reactions.

引用

页码：1835 / 1845

页数：11

共 80 条

[11] Bolm C., 2004, ANGEW CHEM, V116, P6110, DOI DOI 10.1002/ANGE.200460953
[12] Bolm C., 2007, ASYMMETRIC SYNTHESIS, P149, DOI DOI 10.1002/9783527610648.CH2A
[13] Polycyclic Sulfoximines as New Scaffolds for Drug Discovery
Borst, Mark L. G.
Ouairy, Cecile M. J.
Fokkema, Sander C.
Cecchi, Alessandro
Kerckhoffs, Jessica M. C. A.
de Boer, Vincent L.
van den Boogaard, Peter J.
Bus, Rutger F.
Ebens, Rijko
van der Hulst, Rob
Knol, Joop
Libbers, Rob
Lion, Zhou M.
Settels, Bart W.
de Weyer, Ellen
Attia, Khaled A.
Sinnema, Piet-Jan
de Gooijer, Jesse M.
Harkema, Karen
Hazewinkel, Marieke
Snijder, Susan
Pouwer, Kees
[J]. ACS COMBINATORIAL SCIENCE, 2018, 20 (06) : 335 - 343
[14] Straightforward Strategies for the Preparation of NH-Sulfoximines: A Serendipitous Story
Bull, James A.
Degennaro, Leonardo
Luisi, Renzo
[J]. SYNLETT, 2017, 28 (19) : 2525 - 2538
[15] Copper-Catalyzed N-Alkynylations of Sulfoximines with Bromoacetylenes
Chen, Xiao Yun
Wang, Long
Frings, Marcus
Bolm, Carsten
[J]. ORGANIC LETTERS, 2014, 16 (14) : 3796 - 3799
[16] Copper-Catalyzed Oxidative -Ketoacylations of Sulfoximines with Aryl Methyl Ketones and Dioxygen as Terminal Oxidant
Cheng, Hanchao
Bolm, Carsten
[J]. SYNLETT, 2016, 27 (05) : 769 - 772
[17] Palladium-catalyzed α-arylation of sulfoximines
Cho, GY
Bolm, C
[J]. ORGANIC LETTERS, 2005, 7 (07) : 1351 - 1354
[18] Recent Developments in General Methodologies for the Synthesis of α-Ketoamides
De Risi, Carmela
Pollini, Gian Piero
Zanirato, Vinicio
[J]. CHEMICAL REVIEWS, 2016, 116 (05) : 3241 - 3305
[19] Palladium-catalyzed N-vinylation of sulfoximines
Dehli, JR
Bolm, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) : 8518 - 8520
[20] Dey Saibal, 2002, Curr Opin Investig Drugs, V3, P818

← 1 2 3 4 5 6 7 8 →