Asymmetric synthesis of trans-2,5-dimethylpyrrolidine
1993; Elsevier BV; Volume: 4; Issue: 10 Linguagem: Inglês
10.1016/s0957-4166(00)80066-x
ISSN1362-511X
AutoresMariël E. Zwaagstra, Auke Meetsma, Ben L. Feringa,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoA new synthetic route to (2S,5S)-dimethylpyrrolidine 1, which can also be applied to the synthesis of the (2R,5R)-enantiomer, has been developed. The C2-symmetric pyrrolidine can be obtained enantiomerically pure (e.e. ⩾ 97%) in 15% overall yield starting from a mixture of isomers of 2,5-hexanediol, via a short reaction sequence using (S)-α-methylbenzylamine as a chiral auxiliary. The crystal and molecular structure of (S)-2′-phenyl-N-ethyl-(2S,5S)-dimethylpyrrolidine picrate 5, showing an antiparallel stacking of the picrate units, is also reported.
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