Stereochemistry of Reduction of a Heterocyclic α-Hydroxy Ketone. -The stereoselectivity of the reduction of the hydroxyketone (I) using chelating and non-chelating reducing agents is studied. Whilst in most of the cases the syn-diol (II) is formed predominantly, the zinc-chelated DIBAL reduction pr
Stereochemistry of reduction of a heterocyclic α-hydroxy-ketone: The structure, conformation and preparation of the syn and anti-3,3,6,6-tetramethylthiepan-4,5-diols
✍ Scribed by Neil Feeder; Michael J. Ginnelly; Ray V.H. Jones; Susan O'Sullivan; Stuart Warren
- Book ID
- 103399990
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 283 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide enti,anti-1,2,3-triols and syn-1,3-diols, respectively.
## Abstract (±)‐4,5,5‐Trimethyl‐1‐pyrroline‐1‐oxide reacted readily with ethyl 4,5,6,7‐tetra‐__O__‐acetyl‐__trans__‐2,3‐dehydro‐2,3‐dideoxy‐L(−)‐arabinoheptenoate in anhydrous benzene to give a mixture of two diastereomeric isoxazolidines, [2α,3β,3aα,5α]‐ and [2α,3β,3aα,5β]‐ethyl hexahydro‐2‐(1,2,3