Kinetic Resolution, Dynamic Kinetic Resolution and Asymmetric Desymmetrization by N-Heterocyclic Carbene Catalysis

Synthesis ◽  
2019 ◽  
Vol 51 (09) ◽  
pp. 1871-1891 ◽  
Author(s):  
Carmela De Risi ◽  
Olga Bortolini ◽  
Graziano Di Carmine ◽  
Daniele Ragno ◽  
Alessandro Massi

N-Heterocyclic carbenes (NHCs) are now well-established organocatalysts for a large number of asymmetric and non-asymmetric transformations. In the last 15 years, there has been significant interest in using NHCs in kinetic resolution (KR), dynamic kinetic resolution (DKR) and asymmetric desymmetrization reactions for the stereoselective synthesis of enantioenriched compounds, with diverse substrates and activation modes being adopted to this end. This short review brings into focus the progress made on NHC-catalyzed KR, DKR, and asymmetric desymmetrization from 2004 until December 2018. The literature discussed in this article is classified on the basis of the type of reaction involving the NHC catalyst.1 Introduction2 Acylation Strategies2.1 O-Acylation2.2 N-Acylation2.3 C-Acylation3 Aldol-Acylation Processes4 Benzoin Reactions5 Stetter Reactions6 Miscellaneous Approaches7 Conclusion

2004 ◽  
Vol 116 (7) ◽  
pp. 900-902 ◽  
Author(s):  
Kazuishi Makino ◽  
Takayuki Goto ◽  
Yasuhiro Hiroki ◽  
Yasumasa Hamada

2004 ◽  
Vol 43 (7) ◽  
pp. 882-884 ◽  
Author(s):  
Kazuishi Makino ◽  
Takayuki Goto ◽  
Yasuhiro Hiroki ◽  
Yasumasa Hamada

2019 ◽  
Vol 9 (15) ◽  
pp. 4083-4090 ◽  
Author(s):  
Ángela Mourelle-Insua ◽  
Daniel Méndez-Sánchez ◽  
James L. Galman ◽  
Iustina Slabu ◽  
Nicholas J. Turner ◽  
...  

A transaminase-catalyzed dynamic kinetic resolution is described for the stereoselective synthesis of a series of α-alkyl-β-amino amides.


Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1738-1750 ◽  
Author(s):  
Zhuo Chai

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.1 Introduction2 Reaction of Racemic 2-Vinylaziridines3 Reaction of Racemic 2-Alkylaziridines3.1 Regiodivergent Parallel Kinetic Resolution3.2 Kinetic Resolution4 Reaction of Racemic 2-(Hetero)arylaziridines4.1 Kinetic Resolution4.2 Enantioconvergent Transformation5 Reaction of Racemic Donor–Acceptor-Type Aziridines6 Conclusion and Outlook


ChemInform ◽  
2004 ◽  
Vol 35 (22) ◽  
Author(s):  
Kazuishi Makino ◽  
Takayuki Goto ◽  
Yasuhiro Hiroki ◽  
Yasumasa Hamada

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