63006-94-0Relevant academic research and scientific papers
Direct Reductive N-Functionalization of Aliphatic Nitro Compounds
Rauser, Marian,Ascheberg, Christoph,Niggemann, Meike
supporting information, p. 3970 - 3974 (2018/02/26)
The first general protocol for the direct reductive N-functionalization of aliphatic nitro compounds is presented. The nitro group is partially reduced to a nitrenoid, with a mild and readily available combination of B2pin2 and zinc organyls. Thereby, the formation of an unstable nitroso intermediate is avoided, which has so far severely limited reductive transformations of aliphatic nitro compounds. The reaction is concluded by an electrophilic amination of zinc organyls.
Regioselective Transition-Metal-Free Allyl–Allyl Cross-Couplings
Ellwart, Mario,Makarov, Ilya S.,Achrainer, Florian,Zipse, Hendrik,Knochel, Paul
supporting information, p. 10502 - 10506 (2016/08/24)
Readily prepared allylic zinc halides undergo SN2-type substitutions with allylic bromides in a 1:1 mixture of THF and DMPU providing 1,5-dienes regioselectively. The allylic zinc species reacts at the most branched end (γ-position) of the allylic system furnishing exclusively γ,α′-allyl–allyl cross-coupling products. Remarkably, the double bond stereochemistry of the allylic halide is maintained during the cross-coupling process. Also several functional groups (ester, nitrile) are tolerated. This cross-coupling of allylic zinc reagents can be extended to propargylic and benzylic halides. DFT calculations show the importance of lithium chloride in this substitution.
Efficient synthetic method for the preparation of allyl- and propargyl-epoxides by allylation and propargylation of α-haloketones with organozinc reagents
Pan, Jie,Zhang, Min,Zhang, Songlin
, p. 1060 - 1067 (2012/04/10)
A simple, efficient, and non-metal catalyzed synthetic method for the preparation of substituted allyl- and propargyl-epoxides by allylation and propargylation of α-halo ketones with organozinc reagents in mild conditions is reported in this paper. The present method complements the existing synthetic methods due to some advantageous properties of the organozinc reagents such as availability, selectivity, operational simplicity and low toxicity.
A concise and straightforward total synthesis of (±)-salinosporamide A, based on a biosynthesis model
Mulholland, Nicholas P,Pattenden, Gerald,Walters, Iain A. S.
, p. 2782 - 2789 (2009/02/03)
A 14-step total synthesis of (±)-salinosporamide A (1), a potent inhibitor of the 20S proteasome isolated from the marine bacterium Salinospora tropica, is described. The synthesis is based on a diastereoselective intramolecular aldolisation of a substitu
