Regioselective reductive opening of 2,3-epoxy alcohol derivatives with lithium borohydride in a solid state
✍ Scribed by Keisuke Sugita; Makoto Onaka; Yusuke Izumi
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 111 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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## Abstract A simple and mild procedure was developed for the first time for the C(3)‐selective ring opening of an aromatic 2,3‐epoxy alcohol, __i.e.__, of __trans__‐3‐phenyloxirane‐2‐methanol (**1**), with sodium phenoxides or thiophenoxides (=benzenethiolates) **2** supported by __β__‐cyclodextri
Ring-opening b-scission of monocyclic 2-phenyl-1,3-dioxan-2-yl radicals gives preferentially the more stabilised alkyl radical. However, analogous bicyclic radicals derived from two 4,6-O-benzylidene glucopyranosides afford primary radicals in preference to secondary radicals, a result that can be r