Synthesis of enantiopure tertiary skipped diynes via one-pot desymmetrizing TMS-cleavage

Article abstract of DOI:10.1021/ol3017462

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.