1311201-39-4Relevant academic research and scientific papers
Enantioselective synthesis of pyrrolidine-, Piperidine-, and azepane-type N -heterocycles with α-alkenyl substitution: The CpRu-catalyzed dehydrative intramolecular N -allylation approach
Seki, Tomoaki,Tanaka, Shinji,Kitamura, Masato
, p. 608 - 611 (2012/03/10)
A cationic CpRu complex of chiral picolinic acid derivatives [(R)- or (S)-Cl-Naph-PyCOOCH2CH=CH2] catalyzes asymmetric intramolecular dehydrative N-allylation of N-substituted ω-amino- and -aminocarbonyl allylic alcohols with a substrate/catalyst ratio of up to 2000 to give α-alkenyl pyrrolidine-, piperidine-, and azepane-type N-heterocycles with an enantiomer ratio of up to >99:1. The wide range of applicable N-substitutions, including Boc, Cbz, Ac, Bz, acryloyl, crotonoyl, formyl, and Ts, significantly facilitates further manipulation toward natural product synthesis.
A chiral bidentate sp2-N ligand, naph-diPIM: Application to CpRu-catalyzed asymmetric dehydrative C-, N-, and O-allylation
Miyata, Kengo,Kutsuna, Hironori,Kawakami, Sho,Kitamura, Masato
supporting information; experimental part, p. 4649 - 4653 (2011/06/27)
A handy new ligand: The CpRu complex (Cp=cyclopentadienyl) of a new type of chiral bisamidine ligand with a naphtho[1,2-b:7,8-b]dipyrroloimidazole (Naph-diPIM) skeleton with a Bronsted acid efficiently catalyzes dehydrative intermolecular C-allylation with high enantio- and regioselectivity. The catalytic system also gives nearly enantiomerically pure cycloalkanes and N- and O-heterocycles with a substrate/catalyst ratios of up to 10 000.
