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.
Asymmetric carbinol synthesis by means of (−)-sparteine-modified organometallic reagents
✍ Scribed by H. Nozaki; T. Aratani; T. Toraya
- Publisher
- Elsevier Science
- Year
- 1968
- Tongue
- French
- Weight
- 110 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The reactivity of n-butyllithium is enhanced by coordinating tertiary diamines (1:. (_),+~e& ; J_*_Jn,* a 3r L,i#&*>*.&* l&gz3>* &,->*s a, .me&,,i,& ~l&$&~f_3&~, .&LZ.>> jB&s_*a ~~<~mm,*fri)r_ ring ffpprffiibg u? ~-bi~~~~rrocg-clu~~u~~ryl?s i:ezbing tu active sllsaic X+~313rb~'rs <2>.
📜 SIMILAR VOLUMES
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