Enantioselective addition of methyllithium to aromatic imines catalyzed by C2 symmetric tertiary diamines

Understanding Structure Formation in Organolithium Compounds: An Experimental and Quantum‐Chemical Approach

“…Involved solvents were dried with sodium and distilled prior to use. trans ‐TMCDA was synthesized by methylation of the trans ‐amine as described in literature 23 . trans ‐Diaminocyclohexane and 1, 3, 5‐trimethylhexahydro‐1, 3, 5‐triazine were purchased from Aldrich Chemicals.…”

Dichlorido[N,N,N′,N′-tetramethylcyclohexane-1,2-diamine-κ2N,N′]zinc(II)

“…For the use of tetramethylcyclohexane-1,2-diamine in asymmetric addition, see: Cabello et al (2005); Kizirian et al (2005). For related structures, see: Roh et al (2004); Pavlova et al (2003).…”

Reactions of Aldehydes and Ketones and their Derivatives

“…trans-1,2-Diaminocyclohexane ligands have been used as enantioselective catalysts for the asymmetric addition of methyllithium 39 and aryllithiums 40 to aromatic imines. ee A kinetic study of the addition of n-BuLi to a chiral aliphatic aldimine has explored the roles of TMEDA (N ,N ,N ,N -tetramethylethylenediamine) and solvents (toluene, de diethyl ether) on relative rates and diastereoselectivity.…”

“…(S,S)-(+)-Pseudoephedrine proprionamide (39) has been employed as a chiral auxde iliary in asymmetric acetate aldol reactions. 135 A new thioester aldol reaction which uses a half-thioester (PhSOC-*CHMe-CO 2 H) ee of methylmalonic acid and a copper-bis(oxazoline) catalyst is highly enantio-and diastereo-selective, while also being mild and tolerant of protic functional groups and de enolizable aldehydes.…”