Bendelsmith, Andrew J. published the artcileEnantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis, Synthetic Route of 343338-28-3, the main research area is chloro glycinate enantioselective allylation squaramide catalyst allylstannane allylsilane; allyl amino ester chiral preparation.
Chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters is reported. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display 1st-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational anal. of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.
Journal of the American Chemical Society published new progress about Allylation kinetics (stereoselective). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Synthetic Route of 343338-28-3.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics