Asymmetric Vinylogous Mannich‐Type Addition of α,α‐Dicyanoalkenes to α‐Fluoroalkyl Sulfinyl Imines

E-ISSN： 1615-4169|360|2|366-373

ISSN： 1615-4150

Source： ADVANCED SYNTHESIS & CATALYSIS, Vol.360, Iss.2, 2018-01, pp. : 366-373

Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.

Previous Menu Next

Abstract

AbstractThe asymmetric vinylogous Mannich reaction (AVMR) of α,α‐dicyanoalkenes with α‐fluoroalkyl sulfinyl imines has been successfully accomplished. This transformation is unprecedented with fluorinated imines and, at the same time, the use of dicyanoalkenes in AVMR has been scarcely reported. Several fluorinated sulfinyl imines are compatible with the process, which gives access to a family of chiral fluorinated amines with an excellent level of stereocontrol. Interestingly, the selectivity found in our protocol is the opposite of that encountered in analogous, previously reported AVMRs. Additionally, the synthetic applicability of the addition products has been exemplified with several transformations showing the particular reactivity of the dicyanoalkene moiety of these α‐fluorinated amines.