752203-45-5Relevant academic research and scientific papers
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.
Dithiocarbamate group transfer cyclization reactions of carbamoyl radicals under "tin-free" conditions
Grainger, Richard S.,Innocenti, Paolo
, p. 3445 - 3448 (2007/10/03)
Oxygen or nitrogen? Radical chemists overwhelmingly choose to work with xanthates rather than dithiocarbamates, yet the latter offer a distinct advantage in the case of a new method for generating carbamoyl radicals. Functionalized lactams of various ring
