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Direct enantioselective vinylogous Mannich‐type reactions of acyclic enals: New experimental insights into the E/Z ‐dilemma
Author(s) -
Vargiu Michela,
Favero Lucilla,
Menichetti Andrea,
Di Bussolo Valeria,
Marchetti Fabio,
Pescitelli Gennaro,
Di Pietro Sebastiano,
Pineschi Mauro
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23077
Subject(s) - chemistry , enantioselective synthesis , electrophile , organocatalysis , catalysis , dilemma , stereochemistry , computational chemistry , organic chemistry , philosophy , epistemology
The direct heterofunctionalization of acyclic α,β‐unsaturated aldehydes with N‐acylquinolinium ions contemplating the formation of two stereocentres is studied using dienamine catalysis. This work gives some new experimental insights on the remote stereocontrol in dienamine catalysis using unbiased aliphatic systems and large electrophiles, pointing to a ( Z )‐preference of the reactive configuration of the second double bond.