Development of Chiral Potassium Strong Brønsted Base Catalysts for Enantioselective Carbon–Carbon Bond-Forming Reactions

2022 ◽  
Author(s):  
Yasuhiro Yamashita
Keyword(s):  
Enantioselective Catalysis ◽  
Alkaline Metal ◽  
Strong Base ◽  
Carbon Bond ◽  
Bond Forming ◽  
Base Catalysts ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Brønsted Base

Chiral alkaline metal Brønsted bases are traditional and reliable promoters in enantioselective catalysis. Here, new chiral potassium strong base catalysts were developed for enantioselective carbon–carbon bond-forming reactions of weakly acidic...

New Dimensions of Brønsted Base Catalyzed Carbon–Carbon Bond-Forming Reactions

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 14-22
Author(s):  
Yasuhiro Yamashita ◽  
Shū Kobayashi
Keyword(s):  
Addition Reactions ◽  
Alkaline Metal ◽  
Carbon Bond ◽  
Alkaline Metals ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Enantioselective Reactions ◽  
Bond Forming Reactions ◽  
Brønsted Base ◽  
Catalyzed Reactions

Catalytic carbon–carbon bond-forming reactions of weakly acidic carbon pronucleophiles (pK a in DMSO ≥30) were developed using strong alkaline metal Brønsted bases as catalysts. Not only weakly acidic amides, esters, nitriles, sulfonamides without any activating group, and alkyl azaarenes, but also alkyl arenes such as toluene, were applicable for the reactions, which are difficult to be applied in typical Brønsted base catalyzed reactions. Expansion to enantioselective reactions was also revealed to be possible. The reactions are atom economical and require only inexpensive alkaline metals rather than precious transition metals.1 Introduction2 Catalytic Direct-Type Addition Reactions of Weakly Acidic Carbonyl and Related Pronucleophiles3 Catalytic Direct-Type Addition Reactions of Alkyl Azaarenes4 Catalytic Direct-Type Addition Reactions of Alkyl Arenes5 Conclusion

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