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Asymmetric Vinylogous Mannich‐Type Addition of α,α‐Dicyanoalkenes to α‐Fluoroalkyl Sulfinyl Imines
Author(s) -
SanzVidal Álvaro,
Torres Javier,
Soloshonok Vadim A.,
Zhu Yi,
Han Jianlin,
Fustero Santos,
del Pozo Carlos
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701284
Subject(s) - chemistry , moiety , selectivity , combinatorial chemistry , reactivity (psychology) , mannich reaction , enantioselective synthesis , organic chemistry , stereochemistry , catalysis , medicine , alternative medicine , pathology
The 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.