School of Chemistry and Chemical Engineering,
Nanjing University, Nanjing 210093, China.
Yu Wang
School of Chemistry and Chemical Engineering,
Nanjing University, Nanjing 210093, China.
Shengzhou Jin
School of Chemistry and Chemical Engineering,
Nanjing University, Nanjing 210093, China.
Anis U. Rahman
Department of Chemistry and Biochemistry,
Texas Tech University, Lubbock, TX 79409-1061, USA.
Xianghua Yan
Department of Chemistry and Biochemistry,
Texas Tech University, Lubbock, TX 79409-1061, USA.
Qingkai Yuan
Department of Chemistry and Biochemistry,
Texas Tech University, Lubbock, TX 79409-1061, USA.
Hao Liu
Department of Chemistry and Biochemistry,
Texas Tech University, Lubbock, TX 79409-1061, USA.
Jia-Yin Wang
School of Pharmacy, Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry,
Changzhou University, Changzhou, Jiangsu 213164, China.
Wenxin Yan
School of Chemistry and Chemical Engineering, Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education,
Hunan University of Science and Technology, Xiangtan, Hunan 411201, China.
Yinchun Jiao
School of Chemistry and Chemical Engineering, Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education,
Hunan University of Science and Technology, Xiangtan, Hunan 411201, China.
Ruibin Liang
Department of Chemistry and Biochemistry,
Texas Tech University, Lubbock, TX 79409-1061, USA.
Guigen Li
School of Chemistry and Chemical Engineering,
Nanjing University, Nanjing 210093, China.
A series of new targets containing 3 chiral elements of central, orientational, and turbo chirality have been designed and synthesized asymmetrically. The absolute configurations and conformations of these types of chirality were concurrently controlled by using chiral sulfonimine auxiliary and unambiguously determined by x-ray diffraction analysis. These targets include alpha unnatural amino acid derivatives, which may play an important role for drug design, discovery, and development. Three propellers of turbo framework are covalently connected to a chiral C(sp3) center via C(sp2)–C(sp3) bonding along with a C–N axis, while one of them is orientated away from the same carbon chiral center. The turbo or propeller chirality is characterized by 2 types of molecular arrangements of propellers, clockwise (PPP) and counterclockwise (MMM), respectively. The turbo stereogenicity was found to depend on the center chirality of sulfonimine auxiliary instead of the chiral C(sp3) center, i.e., (S)- and (R)-sulfinyl centers led to the asymmetric formation of PPP- and MMM-configurations, respectively. Computational studies were conducted on relative energies for rotational barriers of a turbo target along the C–N anchor and the transition pathway between 2 enantiomers meeting our experimental observations. This work is anticipated to have a broad impact on chemical, biomedical, and materials sciences in the future.
