1373492-68-2Relevant academic research and scientific papers
Carbamoyl radical-mediated synthesis and semipinacol rearrangement of β-lactam diols
Betou, Marie,Male, Louise,Steed, Jonathan W.,Grainger, Richard S.
, p. 6505 - 6517 (2014/06/09)
In an approach to the biologically important 6-azabicyclo[3.2.1]octane ring system, the scope of the tandem 4-exo-trig carbamoyl radical cyclization - dithiocarbamate group transfer reaction to ring-fused β-lactams is evaluated. β-Lactams fused to five-,
Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams
Grainger, Richard S.,Betou, Marie,Male, Louise,Pitak, Mateusz B.,Coles, Simon J.
, p. 2234 - 2237 (2012/06/30)
The 6-azabicyclo[3.2.1]octane ring system, prevalent in a range of biologically active molecules, is prepared through a novel semipinacol rearrangement utilizing a cyclic phosphorane or sulfite intermediate. The rearrangement proceeds with exclusive N-acyl group migration of a β-lactam ring and results in carbonyl functionality at the 7- and bridging 8-position of the bicycle. Precursor ring-fused β-lactam diols are prepared through a sequence of 4-exo trig carbamoyl radical cyclization, regioselective dithiocarbamate group elimination, and dihydroxylation.
