Discovery and organocatalytic enantioselective construction of axially chiral cyclohexadienylidene skeletons

Zhu，Shuai1,2; Mao，Jian Hui2; Cheng，Jun Kee2; Xiang，Shao Hua2,3; Tan，Bin2

2022-09-08

10.1016/j.chempr.2022.06.014

Chem   Impact Factor & Quartile

2451-9308

2451-9294

Studies of axial chirality have advanced to become an integral part of modern chemistry research, especially in asymmetric catalysis. Most investigations have revolved around catalytic enantioselective construction of the privileged axially chiral scaffolds, whereas the discovery of alternative scaffolds lags far behind. Described here is the exploitation of axially chiral molecules that are derived by substituting one C=C double bond of allenes with a cyclohexadienyl moiety. Structurally diverse analogs could be accessed in high efficiency with excellent stereocontrol through two facile and direct synthetic strategies, namely CPA-catalyzed asymmetric dearomatization strategy and enantioselective condensation strategy. Notably, the sterically bulky CPA catalyst plays a central role in the extraordinary levels of chemo-, site-, and enantioselectivities of the dearomatization strategy. These findings not only expand the current library of axially chiral compounds but also offer additional insights to explore other axially chiral scaffolds with different skeletal frameworks.

axial chirality catalytic asymmetric dearomatization chiral phosphoric acid cyclohexadienylidene enantioselective condensation organocatalysis SDG3: Good health and well-being.

English

Corresponding

Guangdong Provincial Key Laboratory Of Catalysis[2020B121201002];National Natural Science Foundation of China[21825105];National Natural Science Foundation of China[21901105];

2-s2.0-85137292354

Scopus

1.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150001,China
2.Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
3.Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen,China

Zhu，Shuai,Mao，Jian Hui,Cheng，Jun Kee,et al. Discovery and organocatalytic enantioselective construction of axially chiral cyclohexadienylidene skeletons[J]. Chem,2022,8(9):2529-2541.

Zhu，Shuai,Mao，Jian Hui,Cheng，Jun Kee,Xiang，Shao Hua,&Tan，Bin.(2022).Discovery and organocatalytic enantioselective construction of axially chiral cyclohexadienylidene skeletons.Chem,8(9),2529-2541.

Zhu，Shuai,et al."Discovery and organocatalytic enantioselective construction of axially chiral cyclohexadienylidene skeletons".Chem 8.9(2022):2529-2541.