Stereoselective Synthesis of Sphinganine by Means of Modified Asymmetric Borane Reduction. -A modified asymmetric borane reduction of the ester (I) and the related silyl ether (V) are described. Thus, reduction of the ester yields mainly the threo compound, whereas the silyl ether affords the desir
Stereoselective synthesis of sphinganine by means of modified asymmetric borane reduction
β Scribed by Moriyasu Masui; Takayuki Shioiri
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 141 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Efficient stereoselective synthesis of sphinganine by the asymmetric borane reduction of ctoxoketoxime trityl ethers is described. Both threo and erythro sphinganine could be obtained with high enantioselectivities by using borane-N,N-diethylaniline complex as a reducing agent.
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## Abstract The enantioselective reduction of ketones was accomplished by borane in the presence of pyrazole derivatives, particularly 2βmethoxymethylβ3βphenylβ1βmenthopyrazole (8). The catalysis of zinc chloride makes it possible to lower the reaction temperature below 0 Β°C, and to promote enantio
## Abstract The equimolar mixture of __N__β(hydroxyalkyl)pyrazoles and borane formed boric ester complex, in which the remaining borane was stabilized by the adjacent nitrogen of thr pyrazole ring. The borane complex derived from the chiral pyrazoles such as 3βphenylβ__l__βmenthopyrazole reduced __