6533b854fe1ef96bd12af350
RESEARCH PRODUCT
Asymmetric Vinylogous Mannich-Type Addition of α,α-Dicyanoalkenes to α-Fluoroalkyl Sulfinyl Imines
Vadim A. SoloshonokVadim A. SoloshonokAlvaro Sanz-vidalJavier TorresYi ZhuCarlos Del PozoSantos FusteroJianlin Hansubject
010405 organic chemistryStereochemistryChemistryMoietyReactivity (chemistry)General Chemistry010402 general chemistrySelectivity01 natural sciencesMedicinal chemistryMannich reaction0104 chemical sciencesdescription
Abstract. The asymmetric vinylogous Mannich reaction (AVMR) of alfa,alfa-dicyanoalkenes with alfa-fluoroalkyl sulfinyl imines has been successfully accomplished. This transformation is unprecedented with fluorinated imines at the same time as the use of dicyanoalkenes in AVMR has been scarcely reported. Several fluorinated sulfinyl imines are compatible with the process, which gaves access to a family of chiral fluorinated amines with excellent level of stereocontrol. Interestingly, the selectivity found in our protocol is reverse to that encountered in analogous AVMR previously reported. Additionally, the synthetic applicability of the addition products has been exemplified with several transformations showing the particular reactivity of the dicyanoalkene moiety of these alfa-fluorinated amines.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-01-10 | Advanced Synthesis & Catalysis |