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First asymmetric synthesis of (2R, 3R)-3-amino-1-benzyl-2-methyl-pyrrolidine via a highly diastereoselective reductive alkylation

✍ Scribed by Pei Qiang Huang; Si Li Wang; Hong Zheng; Xiang Su Fei

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
117 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first asymmetric synthesis of (2R, 3R)-3-amino-l-benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, from (S)-malic acid was achieved via a highly diastereroselective reductive alkylation.

πŸ“œ SIMILAR VOLUMES

Corrigendum to β€œFirst asymmetric synthes
Corrigendum to β€œFirst asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine via a highly diastereoselective reductive alkylation”: [Tetrahedron Letters, 38 (1997), 271]
✍ Pei Qiang Huang; Shi Li Wang; Hong Zheng; Xiang Su Fei πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 31 KB

The authors regret that on page 271 the second author name was spelt incorrectly and should read as ''Shi Li Wang''. ## The value for [h] D of compound 6 on page 271 is also incorrect and should read as follows: [h] D 20 -83.9 (c 1.1 in CHCl 3 ).

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Asymmetric Syntheses via Heterocyclic Intermediates, XLIV. Asymmetric Synthesis of Methyl (2R,3S)-2-Amino-3-cyclopropyl-3-hydroxyalkanoates via Diastereoselective Simmons-Smith Reactions
✍ Groth, Ulrich ;SchΓΆllkopf, Ulrich ;Tiller, Thomas πŸ“‚ Article πŸ“… 1991 πŸ› John Wiley and Sons 🌐 English βš– 465 KB

## Abstract The cyclopropanation of the bislactim ethers 3 with diiodomethanes and diethylzinc proceeds in good yields and with high diastereoselectivities, affording the cyclopropyl bislactim ethers 6. Protection of the hydroxy group and subsequenthydrolysis furnish virtually enantiomerically and