Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic N-Sulfonyl Ketimines by Using N-Heteroarenesulfonyl Cinchona Alkaloid Amides

被引：78

作者：

Nakamura, Shuichi ^{[1
]}

Sano, Masahide ^{[1
]}

Toda, Ayaka ^{[1
]}

Nakane, Daisuke ^{[1
]}

Masuda, Hideki ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 10期

关键词：

enantioselectivity; Mannich reaction; organocatalysis; quaternary stereocenters; CATALYZED ASYMMETRIC ARYLATION; PALLADIUM PINCER COMPLEXES; C BOND FORMATION; MANNICH REACTION; SUPERIOR ELECTROPHILES; NUCLEOPHILIC-ADDITION; PRACTICAL SYNTHESIS; SULTAM AUXILIARIES; 3+2 CYCLOADDITION; BROAD SCOPE;

D O I：

10.1002/chem.201406270

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half thioesters (MAHTs) with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. The reaction proceeds through a nucleophilic addition of the MAHTs to the ketimines prior to decarboxylation.

引用

页码：3929 / 3932

页数：4

共 8 条

[1] Organocatalytic Enantioselective Conjugate Addition of Malonic Acid Half Thioesters to Coumarin-3-carboxylic Acids Using N-Heteroarenesulfonyl Cinchona Alkaloid Amides
Nakamura, Shuichi
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[2] Enantioselective Synthesis of AG-041R by using N-Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts
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[3] Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes
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[4] Organocatalytic enantioselective Mukaiyama-Mannich reaction of fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines
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[J]. ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (03): : 298 - 303
[5] Enantioselective Mannich Reaction between Cyclic N-Sulfonyl Ketimines and Isatin-Derived Ketimines
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13272 - 13283
[6] Enantioselective reaction of N-cyano imines: decarboxylative Mannich-type reaction with malonic acid half thioesters
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[J]. CHEMICAL COMMUNICATIONS, 2022, 58 (13) : 2172 - 2175
[7] Organocatalytic Enantioselective Synthesis of Polycyclic Benzosultams from 2-Amino-β-nitrostyrenes with Cyclic N-Sulfonyl Ketimines
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[J]. ORGANIC LETTERS, 2024, 26 (07) : 1472 - 1477
[8] Highly Enantioselective Decarboxylative Mannich Reaction of Malonic Acid Half Oxyesters with Cyclic Trifluoromethyl Ketimines: Synthesis of β-Amino Esters and Anti-HIV Drug DPC 083
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[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (47) : 15856 - 15860

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