New Chiral Ligands Derived from (S)-Leucine for the Enantioselective Addition of Diethylzinc to Aldehydes
β Scribed by Yasuhiro Kawanami; Tomoko Mitsuie; Misuzu Miki; Takanobu Sakamoto; Kazumi Nishitani
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 94 KB
- Volume
- 56
- Category
- Article
- ISSN
- 0040-4020
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π SIMILAR VOLUMES
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
Optically active amino thioacetate derivatives of (+l-norephedrine were found to act as effective catalysts for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with e.e. of up to >99%.