Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives

Li, Shaoyu1,2,3; Zhang, Ji-Wei1; Li, Xian-Lin1; Cheng, Dao-Juan1; Tan, Bin1

2016-12-21

10.1021/jacs.6b11435

Journal of the American Chemical Society   影响因子和分区

0002-7863

Axially chiral 1,1'-spirobiindane-7,7'-diol (SPINOL) is the most fundamental and important privileged structure from which other chiral ligands containing a 1,1'-spirobiindane backbone are synthesized. Driven by the development of enantioselective syntheses of axially chiral SPINOL derivatives, we have successfully developed the first phosphoric acid-catalyzed asymmetric approach. This approach is highly convergent and functional group tolerant, efficiently providing SPINOLs in good yield with excellent enantioselectivity, thus delivering a practical and straightforward access to this privileged structure. It should be emphasized that the catalyst loading could be decreased to only 0.1 mol% for the preparative-scale synthesis. Furthermore, 4,4'-dimethyl-SPINOL-phosphoric acid was synthesized and applied to catalyze the model reaction for synthesis of enantioenriched SPINOL derivatives.

SCI ; EI ; IC ; CCR

英语

NI论文

第一 ; 通讯

Shenzhen special funds for the development of biomedicine, Internet, new energy, and new material industries[JCYJ20150430160022510]

Chemistry

Chemistry, Multidisciplinary

WOS:000390729500055

AMER CHEMICAL SOC

20165203182577

Catalysis ; Enantioselectivity ; Ligands

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Inorganic Compounds:804.2

Web of Science

1.South Univ Sci & Technol China, Dept Chem, Shenzhen 518055, Peoples R China
2.Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
3.Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

Li, Shaoyu,Zhang, Ji-Wei,Li, Xian-Lin,et al. Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives[J]. Journal of the American Chemical Society,2016,138(50):16561-16566.

Li, Shaoyu,Zhang, Ji-Wei,Li, Xian-Lin,Cheng, Dao-Juan,&Tan, Bin.(2016).Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives.Journal of the American Chemical Society,138(50),16561-16566.

Li, Shaoyu,et al."Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives".Journal of the American Chemical Society 138.50(2016):16561-16566.