𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Highly anti-diastereoselective reduction of 2-alkyl-3-oxo amides by potassium triethylborohydride

✍ Scribed by Yoshio Ito; Tsutomu Katsuki; Masaru Yamaguchi

Book ID
104228926
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
241 KB
Volume
26
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Potassium triethylborohydride was found to reduce 2-alkyl-3-oxo amides to the corresponding 3-hydroxy amides with excellent anti-diastereoselectivity 099:1), and in combination with asymmetric acylation, a useful route to optically active anti-2-alkyl-3-hydroxy acids was developed.

We recently reported an asymmetric acylation of amide enolates 1) where trans-2,5-bis(methoxymethoxymethyl)pyrrolidine 2) served as an efficient chiral

πŸ“œ SIMILAR VOLUMES

First asymmetric synthesis of (2R, 3R)-3
First asymmetric synthesis of (2R, 3R)-3-amino-1-benzyl-2-methyl-pyrrolidine via a highly diastereoselective reductive alkylation
✍ Pei Qiang Huang; Si Li Wang; Hong Zheng; Xiang Su Fei πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 117 KB

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.