663619-22-5Relevant articles and documents
Synthesis of Optically Pure Highly Functionalized γ-Lactams via 2-Azetidinone-Tethered Iminophosphoranes
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.
, p. 993 - 996 (2004)
A synthesis of optically pure densely functionalized γ-lactams starting from 2-azetidinone-tethered iminophosphoranes has been developed. Full chirality transfer has been accomplished from the enantiomerically pure 2-azetidinones. The addition of lithium acetylides to 4-oxoazetidine-2-carbaldehydes at -78 °C smoothly yielded propargylic alcohols with excellent diastereoselectivities. Propargylic alcohols were converted to mesylates, which by exposure to sodium azide afforded the corresponding azides. Treatment of β-lactams bearing an azido side chain with triphenylphosphine (TPP) gave λ5-phosphazenes (iminophosphoranes, phosphine imines), which were not isolated. The sodium methoxide promoted reaction of the phosphazene β-lactams smoothly provided γ-lactams, through a N1-C2 bond breakage process on the four-membered lactam with concomitant ring expansion, followed by hydrolysis.