The reduction of 5,6-dihydro-211-1,3-oxazines 2 is described for the first time.This reaction allows the diastereoselective synthesis of 1,3-amino alcohols 3 and 4 with three and four chiral centers.
Simple synthesis of 2H-1,3-oxazines and their stereoselective transformation into 1,3-aminoalcohols and azetidines
✍ Scribed by José Barluenga; Miguel Tomás; Alfredo Ballesteros; Jian-She Kong
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 600 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0040-4020
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## Abstract 6__H__‐1,2‐Oxazines 1 and 3 are converted into aziridines 2 and 4, respectively, by reduction with LiAlH~4~. Reduction of 1,2‐oxazine 5 lacking the 6‐alkoxy substituent leads to phenyl ketone 6, 6‐Alkoxy‐substituted 1,2‐oxazine‐3‐carboxylates 7, 9, and 11 are reduced with NaBH~4~ to giv