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Efficient general synthesis of 1,2- and 1,3-Diols in high enantiomeric excess via the intramolecular asymmetric reduction of the corresponding ketoalkyl diisopinocampheylborinate intermediates
The first successful asymmetric reduction of unhindered aliphatic ketones with B-chlorodiisopinocampheylborane is reported. In contrast to the reduction in high ee of aralkyl ketones, such as acetophenone, with the reagent, the reduction of unhindered dialkyl ketones, such as 3-methyl-2-butanone, provides only poor ee. However, treatment of alpha- and beta-hydroxyketones with one equiv of diisopnocampheylborane or B-chlorodiisopinocampheylborane rapidly produces the corresponding ketoalkyl diisopinocampheylborinate intermediates, which then undergo facile intramolecular reduction. This reaction sequence, followed by oxidative workup, provides a general synthesis of 1,2- and 1,3-diols in 84?99% enantiomeric excess.
Safety of (S)-Propane-1,2-diol, Each elementary reaction can be described in terms of its molecularity, the number of molecules that collide in that step. The slowest step in a reaction mechanism is the rate-determining step.you can also check out more blogs about Safety of (S)-Propane-1,2-diol
Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate