Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines

A simple and efficient asymmetric synthesis of novel sp3 rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesulfinamide as a chiral auxiliary to perform an asymmetric Tsuji-Trost allylation, with subsequent cross-metathesis with an acrylate ester and reduction of the sulfinimine/cyclisation of the resulting amine giving the pyrrolidine scaffolds in high yields and diastereoselectivites. By removing the chiral auxiliary and functionalising the ester group, the resulting scaffold core can be further derivatised

Facile access to a heterocyclic, sp3-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy

A heterocyclic, sp3-rich chemical scaffold was synthesised in just 6 steps via a highly regio- and diastereo-selective tandem nitrone formation/intramolecular nitrone–alkene [3+2] cycloaddition reaction. A library of 543 lead-like compounds based on the scaffold core has been produced

Stereoretentive Pd-Catalyzed Kumada–Corriu Couplings of Alkenyl Halides at Room Temperature

Stereoselective palladium-catalyzed Kumada–Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, <i>including those bearing β-hydrogen atoms and sensitive functional groups</i>, can be carried out at room temperature using a new combination of reagents

Total Synthesis of Coibacin D by Using Enantioselective Allylation and Metathesis Reactions

The first asymmetric total synthesis of coibacin D, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp., was achieved in six steps starting from simple hept‐6‐en‐1‐ol. The synthetic strategy was based on a chiral Brønsted acid catalyzed enantioselective allylboration and a Ru‐carbene complex catalyzed sequential ring‐closing and cross‐metathesis strategy. The recorded spectroscopic data and the sign of the optical rotation of the synthesized coibacin D were in agreement with the published data for the isolated compound, which confirmed the proposed structure and absolute configuration.Allyl be done in six: Coibacin D was synthesized in six steps from 6‐hepten‐1‐ol by using a chiral Brønsted acid catalyzed enantioselective allylation, a ring‐closing metathesis, a cross‐metathesis, and electrophilic chlorination reactions as the crucial key steps. The characterization data of the synthesized product were in agreement those of the isolated compound, which confirmed the proposed structure and absolute configuration.Peer Reviewedhttps://deepblue.lib.umich.edu/bitstream/2027.42/137328/1/ajoc201600022_am.pdfhttps://deepblue.lib.umich.edu/bitstream/2027.42/137328/2/ajoc201600022-sup-0001-misc_information.pdfhttps://deepblue.lib.umich.edu/bitstream/2027.42/137328/3/ajoc201600022.pd