ChemInform Abstract: Catalytic Enantioselective Reactions. Part 7. Synthesis of New β- Aminoalcohols Derived from α-D-Glucose as Chiral Catalysts for the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes.
✍ Scribed by B. T. CHO; N. KIM
- Book ID
- 112033584
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 31 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0931-7597
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Secondary amines react with (IR,2S)-indene oxide 1 in a completely regioselective manner leading to trans-2-dialkylamino-l-indanols 4a-d in high yield. A Mitsunobu inversion via the corresponding p-nitrobenzoates, followed by reduction with DIBALH leads to the cis-2-dialkylamino-l-indanols 5a-d also
The enantioselective additionof diethylxinc to ztldehydes using 1,2-isopropylidene-Sdeoxy-5-dialkylammO-U-D-XylOfuranOse8 derived from a-D-xylose as new catalysts provided the corresponding alcohlos with 75-96 % ee. Enantioselective addition of diethylzinc to aldehydes by chiral ligands is a conven