Sodium bis(2-methoxyethoxy)(1,1,1,3,3,3-hexafluoro-2-propoxy)aluminum hydride, a new stereoselective reducing agent in a carbacyclin synthesis
โ Scribed by Susumu Harashima; Osamu Oda; Shigeo Amemiya; Koichi Kojima
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 793 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
A new reducing agent (2j) reduced the enone (4) to give 15(S)-allylic alcohol (5a) with excellent regio-and stereoselectivity through a five membered ring transition state. Stereoselectivity of this reaction will be explained based on the LUMO of the enone moiety. The resulting (5a) was led to a carbacyclin.
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The 1,1,1,3,3,3-Hexafluoro-2-propyl group can be used as a new class of phosphate protecting group for the protecting group of internucleotidic bonds in the oligonucleotide synthesis by the phosphotriester approach . This protecting group is removed easily by treatment with 0 .3 M N 1 ,N 1 ,N 3 ,N''
a-(Hydroxymethyl)allyl tolylsulfones reacted with tributyltin hydride in the presence of azobisisobutyronitrile(AIBN) in refluxing benzene to give a allyltin derivatives which subsequently gave 2-substituted-1,3-butadienes upon distillation in good yield.