Highly Enantio- and Diastereoselective Mannich Reactions of Chiral Ni(II) Glycinates with Amino Sulfones. Efficient Asymmetric Synthesis of Aromatic α,β-Diamino Acids

2008 ◽  
Vol 73 (21) ◽  
pp. 8563-8570 ◽  
Author(s):  
Jiang Wang ◽  
Ting Shi ◽  
Guanghui Deng ◽  
Hualiang Jiang ◽  
Hong Liu
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reactions

Asymmetric Synthesis of α‐Difluorinated β‐Amino Sulfones via Detrifluoroacetylative Mannich Reactions

2021 ◽  
Author(s):  
Ziyi Li ◽  
Nana Wang ◽  
Haibo Mei ◽  
Hiroyuki Konno ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reactions

Direct enantioselective Mannich reactions of α-azido cyclic ketones: asymmetric construction of chiral azides possessing an α-quaternary stereocenter

2020 ◽  
Vol 56 (1) ◽  
pp. 98-101 ◽  
Author(s):  
Xueqian Ye ◽  
Yongkai Pan ◽  
Xiaoyu Yang
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Cyclic Ketones ◽  
Mannich Reactions ◽  
Chiral Phosphoric Acid ◽  
Quaternary Stereocenter

Herein, we report the asymmetric synthesis of chiral azides possessing an α-quaternary stereocenter via chiral phosphoric acid catalysed direct enantioselective Mannich reactions of α-azido cyclic ketones with aldimines.

Asymmetric Synthesis of C1-Chiral THIQs with Imines in Isoquinoline Rings

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3337-3355
Author(s):  
Dan Li ◽  
Wei Gao ◽  
Xiaochao Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Biological Activities ◽  
Asymmetric Reactions ◽  
Structural Units ◽  
Mannich Reactions ◽  
Asymmetric Reaction ◽  
Azomethine Imines ◽  
Catalytic Asymmetric ◽  
Further Development ◽  
New Strategies

Tetrahydroisoquinoline (THIQ) scaffolds are important structural units that widely exist in a variety of natural alkaloids and synthetic analogues. Asymmetric synthesis of C1-chiral THIQ is of particular importance due to its significant pharmaceutical, agrochemical, and other biological activities, and the usually distinct bioactivities exhibited by the two enantiomers. In this review, we highlight the significant advances achieved in this field, present recent asymmetric synthesis with imines in isoquinoline rings ordered according to the sequence of various substrate types. New strategies could be inspired and more types of substrates need further development.1 Introduction2 Catalytic Asymmetric Reaction of Dihydroisoquinolines2.1 Asymmetric Reactions of 3,4-Dihydroisoquinolines2.2 Asymmetric Reactions of Dihydroisoquinolinium Salts2.3 Asymmetric Reactions of C,N-Cyclic N′-Acyl Azomethine Imines2.3.1 NED [3+2] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.2 IED [3+2] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.3 [3+3] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.4 [4+3] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.5 Asymmetric Addition Reactions to C,N-Cyclic N′-Acyl Azomethine Imines2.4 Asymmetric Reactions of C,N-Cyclic Nitrones3 Catalytic Asymmetric Mannich Reactions of Isoquinolines4 Conclusions and Perspectives

Asymmetric synthesis of amino-benzothiazol derivatives by additions of 2-lithiated benzothiazoles to (S)-N-t-butylsulfinyl-ketimines

RSC Advances ◽  
2015 ◽  
Vol 5 (5) ◽  
pp. 3491-3497 ◽  
Author(s):  
Yanling Dai ◽  
Chen Xie ◽  
Lingmin Wu ◽  
Haibo Mei ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reactions ◽  
Unknown Type ◽  
Derivatives Of

We reported the asymmetric Mannich reactions between lithium-benzothiazoles and (S)-N-tert-butanesulfinylketimines, which gave unknown type of amino-benzothiazol derivatives of high pharmaceutical potential with up to 96% yields and 99 : 1 diastereoselectivities.

scholarly journals Asymmetric synthesis of δ-amino acid derivatives via diastereoselective vinylogous Mannich reactions between N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate

RSC Advances ◽  
2017 ◽  
Vol 7 (80) ◽  
pp. 50822-50828 ◽  
Author(s):  
Guijun Li ◽  
Xiaoliang Xu ◽  
Hongchang Tian ◽  
Xiaotong Liu ◽  
Wen Chen ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Mannich Reaction ◽  
Amino Acid Derivatives ◽  
Mannich Reactions

A diastereoselective vinylogous Mannich reaction between theN-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate was developed.

Enantioselective Vinylogous Reactions of 3-Alkylidene Oxindoles

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2463-2472 ◽  
Author(s):  
Renato Dalpozzo ◽  
Raffaella Mancuso
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Carbonyl Compounds ◽  
Important Class ◽  
Chiral Molecules ◽  
Research Groups ◽  
Mannich Reactions ◽  
The Creation ◽  
Synthetic Derivatives

Oxindoles represent an important class of bioactive compounds and synthetic derivatives found in many natural products. Most of these compounds are chiral molecules and the challenge of their asymmetric synthesis has fascinated many research groups. In particular, the creation of chiral centers out of the oxindole ring by vinylogous addition to 3-alkylidene-substituted oxindoles (3-alkylidene-1,3-dihydro-2H-indol-2-ones) has emerged in recent years. This review aims to give an overview of this topic.1 Introduction2 Aldol and Mannich Reactions3 Addition to Unsaturated Carbonyl Compounds4 Addition to Nitroalkenes5 Miscellaneous6 Conclusion

Asymmetric synthesis of quaternary α-fluoro-β-keto-amines via detrifluoroacetylative Mannich reactions

2015 ◽  
Vol 51 (44) ◽  
pp. 9149-9152 ◽  
Author(s):  
Chen Xie ◽  
Yanling Dai ◽  
Haibo Mei ◽  
Jianlin Han ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Bond Cleavage ◽  
Mannich Reactions

Asymmetric detrifluoroacetylative Mannich reactions of N-sulfinyl-imines via C–C bond cleavage were explored, which provide access to C–F quaternary α-fluoro-β-keto-amines.

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