(S)-(−)-α-Methylbenzylamine as an efficient chiral auxiliary in enantiodivergent synthesis of both enantiomers of N-acetylcalycotomine

Add time:07/27/2019    Source:sciencedirect.com

(S)-(−)-α-Methylbenzylamine 2 was used as a chiral auxiliary in the enantiodivergent synthesis of simple isoquinoline alkaloids. The prochiral imine moiety in compound 4 was reduced with different reagents, giving diastereomeric amines 5a or 5b, which subsequently were transformed to either (S)-(−)-N-acetylcalycotomine 6 or (R)-(+)-N-acetylcalycotomine ent-6 in good enantiomeric excess. 19F NMR of its Mosher's acid ester was used to establish the purities of final compounds.

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