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Selective Synthesis of Trifluoromethyl β‐Lactams by a Zn‐Promoted 2‐Bromo Ester Addition on C ‐CF 3 ‐Substituted Aldimines
Author(s) -
Trulli Laura,
Raglione Venanzio,
Fioravanti Stefania
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800168
Subject(s) - aldimine , chemistry , trifluoromethyl , zinc , organic chemistry , medicinal chemistry , molar ratio , stereochemistry , catalysis , alkyl
Starting from C ‐CF 3 ‐substituted aldimines, trifluoromethyl β‐lactams were obtained as only products in the reaction with some α‐bromo esters in the presence of activated zinc dust. Different solvents, molar ratios, and temperature were tested to determine the best reaction conditions that led only to desired cyclic compounds. The influence of another ester group on the aldimine chain and the reaction diastereoselectivity were also considered.