ChemInform Abstract: Synthesis of Chiral Alkynes Having 2H or Halogen at the Secondary of Tertiary Propargylic Stereogenic Center by Hydrolysis and Halogenolysis of Optically Active Allenyltitaniums Having Axial Chirality.

✍ Scribed by D. K. AN; S. OKAMOTO; F. SATO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199837069

✦ Synopsis

Optically active allenyltitanium [cf. (III)], generated from propargyl alcohol derivatives in solution, undergoes regioselective hydrolysis and halogenolysis to give the alkyne (IV) and the chloride (V) with excellent degree of chiral transfer. This approach is also successfully applied to the synthesis of secondary propargylic bromide (VII). -(AN, D.