Trifluoromethyl aldimines: an overview in the last ten years

Selective Synthesis of Trifluoromethyl β‐Lactams by a Zn‐Promoted 2‐Bromo Ester Addition on C‐CF3‐Substituted Aldimines

“…Recently, imino‐Reformatsky reactions were developed that start from fluorine‐containing α‐halogenated acetates to obtain fluorinated β‐amino esters and β‐lactams . However, the synthesis of trifluoromethylated compounds by start from trifluoromethyl aldimines remains poorly studied and very few examples have been reported in the literature …”

“…[12] However, the synthesis of trifluoromethylated compounds by start from trifluoromethyl aldimines remains poorly studied [13] and very few examples have been reported in the literature. [14] To the best of our knowledge, only one imino-Reformatsky reaction between 2-bromo acetates and N-p-methoxyphenyl 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.…”

Development and Evaluation of Different Methods for Preparation of Fluorine‐Containing (R)‐ and (S)‐N‐tert‐Butanesulfinyl–aldimines

“…As a convincing testament to the pharmaceutical potential of fluorinated amino‐compounds one can mention Odanacatib ( 1 ) (Figure ), a new drug recently approved for treatment of osteoporosis and bone metastasis . Among various methods for preparation of 2,2,2‐trifluoro‐1‐(amino)ethyl containing compounds, Mannich‐type additions of chiral imines 2 (Figure ) is unarguably the most generalized approach …”

“…N ‐ tert ‐butanesulfinyl‐imines 2 , inspired by the seminal work of Ellman group, [37, 38] possess quite remarkable stereocontrolling properties, high reactivity and can be used for selective and highly efficient installation of 2,2,2‐trifluoro‐1‐(amino)ethyl moiety. As demonstrated by numerous research groups, most notably by O′Shea, Qing, Shibata, [44, 45] Roeschenthaler and Han, CF 3 ‐imines 2 easily react with virtually any type of nucleophiles, including Baylis‐Hillman and Friedel‐Crafts reactions, affording the target 2,2,2‐trifluoro‐1‐(amino)ethyl containing compounds with excellent yields and diastereoselectivity. Considering the wealth of literature data one can assert that chemistry of CF 3 ‐imines 2 is a mature field of a proven, exceptionally high synthetic value.…”

“…[23][24][25] Among various methods for preparation of 2,2,2-trifluoro-1-(amino)ethyl containing compounds, [26][27][28][29][30][31][32] Mannich-type additions of chiral imines 2 ( Figure 1) is unarguably the most generalized approach. [33][34][35][36] N-tert-butanesulfinyl-imines 2, inspired by the seminal work of Ellman group, [37,38] possess quite remarkable stereocontrolling properties, high reactivity and can be used for selective and highly efficient installation of 2,2,2-trifluoro-1-(amino)ethyl moiety. As demonstrated by numerous research groups, [33][34][35][36] most notably by O'Shea, [24,25] Qing, [39][40][41][42][43] Shibata, [44,45] Roeschenthaler [46][47][48][49][50] and Han [51][52][53][54][55] , CF 3 -imines 2 easily react with virtually any type of nucleophiles, including Baylis-Hillman [56] and Friedel-Crafts reactions, [57,58] affording the target 2,2,2-trifluoro-1-(amino)ethyl containing compounds with excellent yields and diastereoselectivity.…”