Tetrahedron p. 12547 - 12560 (1998)
Update date:2022-08-04
Topics:
Huang, Pei Qiang
Wang, Shi Li
Ye, Jian Liang
Ruan, Yuan Ping
Huang, You Qing
Zheng, Hong
Gao, Jing Xing
A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2- pyrrolidinones is described. The key steps involve a regioselective Grignard reagent addition to (S)-malimides, and diastereoselective reductive dehydroxylation of the resulting hemi-azaketals. The flexibility of this methodology has been demonstrated by the synthesis of (2R, 3R)-3-amino-1- benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, and the unnatural enantiomer of the β-hydroxy-γ-amino acid residue of hapalosin in lactam form.
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