Aggregation-Induced Synthesis (AIS): Asymmetric Synthesis via Chiral Aggregates
Hossein Rouh,
Yao Tang,
Ting Xu,
Qingkai Yuan,
Sai Zhang,
Jia-Yin Wang,
Shengzhou Jin,
Yu Wang,
Junyi Pan,
Hannah L. Wood,
James D. McDonald,
Guigen Li
Affiliations
Hossein Rouh
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
Yao Tang
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
Ting Xu
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
Qingkai Yuan
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
Sai Zhang
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
Jia-Yin Wang
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
Shengzhou Jin
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
Yu Wang
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
Junyi Pan
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
Hannah L. Wood
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
James D. McDonald
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
Guigen Li
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA; Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
A new chiral aggregate-based tool for asymmetric synthesis has been developed by taking advantage of chiral aggregates of GAP (Group-Assisted Purification) reagents, N-phosphonyl imines. This tool was proven to be successful in the asymmetric GAP synthesis of functionalized 2,3-dihydrobenzofurans by reacting salicyl N-phosphonyl imines with dialkyl bromomalonates in various cosolvent systems. The chiral induction can be controlled by differentiating between two asymmetric directions simply by changing the ratios of cosolvents which are commonly adopted in AIE (aggregation-induced emission) systems. The formation of chiral aggregates was witnessed by a new analytical tool—aggregation-induced polarization (AIP). The present synthetic method will be broadly extended for general organic synthesis, particularly, for asymmetric synthesis and asymmetric catalysis in the future.
