Synthesis of enantiomerically enriched isotopically-labelled anilines by (−)-sparteine directed lithiation

Anilines bearing benzyl or isopropyl groups isotopically labelled (with 2H or 13C) in one of a pair of enantiotopic protons or methyl groups can be made using (−)-sparteine-directed lithiation with an electrophilic quench, followed by deprotection.

2H and 13C labelled amines were made in enantiomerically enriched form by (−)-sparteine directed benzylic lithiation of carbamates and amides.Figure optionsDownload as PowerPoint slide

N-Benzyl-3,3,3-trifluoro-2-methoxy-N-(4-methoxyphenyl)-2-phenylpropanamideC24H22F3NO3[α]D24=-106 (c 0.4, CH2Cl2)