Regio‐ and Diastereoselective Conjugate Addition of Grignard Reagents to Chiral Fluoroalkyl α,β‐Unsaturated N‐tert‐Butanesulfinyl Ketimines: Synthesis of Optically Active Fluorinated Enamines and Derivatives

• Published in: Advanced synthesis & catalysis Vol. 366; no. 3; pp. 414 - 419
• Main Authors: Ma, Wen‐Jiang, Liu, Peng, Liao, Tian‐Ming, Gao, Yu‐Ning, Bian, Ming, Liu, Jin‐Tao, Wu, Fanhong, Chen, Hui‐Yu, Liu, Zhen‐Jiang
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 19.02.2024; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Applied; Chemistry, Organic; Conjugate addition; Conjugates; Diastereoselective; Fluorinated enamines; Fluorination; Imines; N-tert-Butanesulfinyl ketimine; Optical activity; Physical Sciences; Reagents; Regioselective; Science & Technology; Stereoselectivity; Synthesis; Fluorinated enamines; Regioselective; Diastereoselective; ASYMMETRIC-SYNTHESIS; IMINES; Conjugate addition; N-tert-Butanesulfinyl ketimine
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202300983

A regio‐ and diastereoselective conjugate addition reaction of Grignard reagents to fluoroalkyl α,β‐unsaturated N‐tert‐butanesulfinyl ketimines was disclosed. A range of different fluoroalkyls and Grignard reagents were well tolerated, giving up to 99% diastereomeric and regioisomeric ratios. This reaction provided a straightforward method for the synthesis of a variety of enantiomerically enriched α‐fluorinated enamines and derivatives which are difficult to achieve with other methods.