Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group

Development of Useful Reactions Involving Tandem Cyclizations Based on the Novel Reactivities of Allenic Compounds

“…Although space restriction does not permit a detailed description, our group developed some other interesting novel reactions such as (1) stereoselective synthesis of 1,3-amino alcohols via allenylindium reagents using 2-ethynylaziridines as chiral carbon nucleophiles, 143,144) (2) samarium(II)-mediated radical cyclization onto an aromatic group, [174][175][176][177][178] (3) synthesis and isomerization of vinylaziridines and their application to the stereoselective synthesis of (E)-alkene dipeptide isosteres. [64][65][66][67]179,180) The author hopes the presented reactions based on the novel reactivities of allenes will facilitate further development of allene chemistry [181][182][183] and application to synthesis of pharmacologically important compounds from this class of compounds.…”

Synthesis and Applications of Vinylaziridines and Ethynylaziridines

“…The ring-opening reduction of vinylaziridines can be promoted by a palladium catalyst (Scheme ) . The reduction of aziridines 177 bearing an α,β-unsaturated ester group with formic acid gave 1,2-reduction products 179 together with 1,4-products 180 .…”

Stereoselective synthesis of γ-amino acids

“…371 On the other hand, Mitsunobu reaction of amino alcohol syn-1036 obtained from chiral amino aldehydes gave cis-aziridine 1037, 373 which by ozonolysis followed by the Wittig reaction with (carbomethoxyethylene)triphenylphosphorane produced (E)-alkenyl-aziridine 1038 as the principal product (Scheme 257). 374 This methodology has been used in the synthesis of several (E)-alkenyl-aziridines.…”