94202-79-6Relevant academic research and scientific papers
The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis
Garbacz, Mateusz,Stecko, Sebastian
, p. 3213 - 3222 (2020/07/06)
A mild, and versatile, organophotoredox/Ni-mediated protocol was developed for the direct preparation of diverse, enantioenriched allyl carbamates. The reported approach represents a significant departure from classical step-by-step synthesis of allyl carbamates. This dual photoredox/Ni based strategy offers unrivalled capacity for convergent unification of readily available alkyl halides and chiral carbamates derived from 1-bromo-alken-3-ols with high chemoselectivity and efficiency. The reported photoredox/Ni catalyzed cross-coupling reaction is not limited to carbamates, but also to other O-derivatives such as esters, ethers, acetals, carbonates or silyl ethers. To demonstrate the utility of the reported protocol, the resulting allyl carbamates were transformed into functionalized non-racemic allylamines through a sigmatropic rearrangement reaction in enantiospecific manner. This approach allowed for synthesis of enantiomeric allylamines by a simple control of the geometry of a double bond of allyl carbamates. (Figure presented.).
Asymmetric Carbon to Nitrogen Bond Formation Using Optically Active Allylic Selenides: A New General Method for the Synthesis of N-Protected Optically Active α-Amino Acids
Fitzner, Jeffrey N.,Shea, Regan G.,Fankhauser, John E.,Hopkins, Paul B.
, p. 417 - 419 (2007/10/02)
Optically active allylic selenides undergo oxidative sigmatropic rearrangement to afford optically active, protected allylic amines.The synthetic utility of this process is demonstrated by the synthesis of several N-protected D-α-amino acids in 78-84percent enantiomeric excess.
