Chiral amides

Lithium amides, chiral. Koga et al.x have prepared a series of lithium amides of the type in which one carbon atom adjacent to the nitrogen is chiral and bears a bulky group (phenyl, naphthalene, r-butyl). Highest enantioselective deprotonation... 

Camphor- 10-sulfonic acid, 62 (S)-2-(l-Hydroxy-1-methylethyl)-pyrrolidine, 146 a-Methylbenzylamine, 185 Quina alkaloids, 264 Cycloaddition reactions 2-Oxazolidones, chiral, 225 Cyclopropanation Diiodomethane-Diethylzinc, 276 Simmons-Smith reagent, 275 Deprotonation Lithium amides, chiral, 159... 

SlLYL ENOL ETHERS Chiorotrimethylsilane-Zinc, 82 Lithium amides, chiral, 159 Lithium tri-sec-butylborohydride, 167 Organotin reagents, 211 Osmium tetroxide-Trimethylamine N-ox-ide-Pyridine, 223... 

Ethylenediamine, 157 Hexamethyldisilazane, 175, 331 Isopropylamine, 164 N-Lithioethylenediamine, 157, 200 Lithium amides, chiral, 159 Lithium 3-aminopropylamide, 157, 160 Lithium 3-aminopropylamide-Potas-sium /-butoxide, 160 Lithium dicyclohexylamide, 110 Lithium diisopropylamide, 106, 143, 148, 163, 188, 256, 257, 326 Lithium diisopropylamide-Hexa-methylphosphoric triamide, 143, 172 Lithium diisopropylamide-Potassium t-butoxide, 164... 

Lithium amides, chiral, 159 Lithium isopropyl[ 2-(4-methylpipera-zyl)-l-phenylethyl] amide, 160 Chiral Boranes... 

Variable levels of asymmetric induction or diastereoselectivity have been found with additions of or-ganometallics to a,0-unsaturated chiral amides (chiral auxiliary). For example, as shown in Scheme 26, Mukaiyama reports that the diastereoselective addition of Grignard reagents to -substituted a,p-un-... 

In 2004, Walsh s group developed L-proline-catalysed aldol reactions of atropisomeric amides sueh as benzamides and naphthamides. " The DKR process simultaneously established the stereoehemistry of the atropisomeric amide chiral axis and a stereogenic centre, providing high enantioselectivities, as shown in Scheme 2.101. 

Davis FA, Qi HY, Sundarababu G. Application of oxazoUdi-none a-fluoro amide chiral building blocks in the asymmetric synthesis of fluorinated carbohydrates 2-deoxy-2-fluoropentoses. Tetrahedron 2000 56 5303-5310. 

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