1313870-25-5Relevant articles and documents
Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants
Breugst, Martin,Cao, Jing,Gillard, Rachel,Jahanbakhsh, Azar,Lupton, David W.
, p. 11791 - 11796 (2020/11/27)
An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of
Oxidative NHC catalysis: direct activation of β sp3 carbons of saturated acid chlorides
Zhu, Shi-Ya,Zhang, Hua,Ma, Qing-Wei,Liu, Dou,Hui, Xin-Ping
supporting information, p. 298 - 301 (2019/01/09)
The first activation of saturated acid chlorides by oxidative N-heterocyclic carbene catalysis has been successfully utilized to synthesize enantio-enriched spirooxindole lactones and δ-lactones. The reaction involves the transformation of the β sp3 carbon of saturated acid chlorides into an electrophilic carbon as a key step. The product was obtained in excellent yield and stereoselectivity.
Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for α, β-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions
Gao, Yaru,Ma, Yafei,Xu, Chen,Li, Lin,Yang, Tianjian,Sima, Guoqing,Fu, Zhenqian,Huang, Wei
, p. 479 - 484 (2017/12/26)
Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for α,β-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-handle solid salts could release of CO2 and then undergo asymmetric reactions via homoenolate and α, β-unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities. (Figure presented.).
