Synthesis of Enantiopure tertiary skipped diynes via one-pot desymmetrizing TMS-cleavage.
Enantiopure tetrasubstituted skipped diynes were readily synthesized from N-protected amino esters upon addition of lithium TMS-acetylide which was found to be desymmetrizing through one-pot selective TMS-cleavage. The deprotection of the TMS group was realized through a one-pot silicon atom attack by the liberated methoxide, which was diastereoselective due to a conformational favorable chelate.
Aix-Marseille Université, CNRS, ICR, UMR 7273, 13397 Cedex 20, Marseille, France. malek.nechab@univ-amu.fr
Malek
M
Nechab
Nicolas
N
Vanthuyne