Stereoselective Synthesis of Bicyclic Tertiary Alcohols with Quaternary Stereocenters via Intramolecular Crossed Benzoin Reactions Catalyzed byN-Heterocyclic Carbenes

2009 ◽  
Vol 11 (21) ◽  
pp. 4866-4869 ◽  
Author(s):  
Tadashi Ema ◽  
Yoshitaka Oue ◽  
Kumiko Akihara ◽  
Yuki Miyazaki ◽  
Takashi Sakai
Keyword(s):  
Stereoselective Synthesis ◽  
Heterocyclic Carbenes ◽  
Tertiary Alcohols ◽  
Quaternary Stereocenters

Oxidation of chiral α-phenylacetate derivatives: formation of dimers with contiguous quaternary stereocenters versus tertiary alcohols

2005 ◽  
Vol 16 (21) ◽  
pp. 3599-3605 ◽  
Author(s):  
Marisa C. Kozlowski ◽  
Evan S. DiVirgilio ◽  
Krishnan Malolanarasimhan ◽  
Carol A. Mulrooney
Keyword(s):  
Tertiary Alcohols ◽  
Quaternary Stereocenters

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
Keyword(s):  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Short Review ◽  
Heterocyclic Carbenes ◽  
Dynamic Kinetic Resolution ◽  
Asymmetric Transformations ◽  
Significant Interest ◽  
Stetter Reactions

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

ChemInform Abstract: A New Stereoselective Synthesis of Cyclopropanes Containing Quaternary Stereocenters via Organocatalytic Michael Addition to Vinyl Selenones.

ChemInform ◽  
2010 ◽  
Vol 41 (2) ◽  
Author(s):  
Francesca Marini ◽  
Silvia Sternativo ◽  
Francesca Del Verme ◽  
Lorenzo Testaferri ◽  
Marcello Tiecco
Keyword(s):  
Michael Addition ◽  
Stereoselective Synthesis ◽  
Quaternary Stereocenters

scholarly journals N-Heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis

2012 ◽  
Vol 8 ◽  
pp. 398-402 ◽  
Author(s):  
Rob De Vreese ◽  
Matthias D’hooghe
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Stereoselective Synthesis ◽  
Heterocyclic Carbenes ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Heterocyclic Chemistry ◽  
The Past ◽  
Cooperative Catalysis ◽  
Brönsted Acid

The interplay between metals and N-heterocyclic carbenes (NHCs) has provided a window of opportunities for the development of novel catalytic strategies within the past few years. The recent successful combination of Brønsted acids with NHCs has added a new dimension to the field of cooperative catalysis, enabling the stereoselective synthesis of functionalized pyrrolidin-2-ones as valuable scaffolds in heterocyclic chemistry. This Commentary will briefly highlight the concept of N-heterocyclic carbene/Brønsted acid cooperative catalysis as a new and powerful methodology in organic chemistry.

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