438620-40-7Relevant academic research and scientific papers
Retention of chirality of 5-membered alicyclic α-amino acids bearing N-(2-phenyl)benzoyl group in photoinduced decarboxylative intermolecular radical addition to acrylonitrile
Ozaki, Yui,Yamada, Tomoaki,Mizuno, Taisei,Osaka, Kazuyuki,Yamawaki, Mugen,Maeda, Hajime,Morita, Toshio,Yoshimi, Yasuharu
, (2019/08/08)
Photoinduced decarboxylative radical additions of 5-membered alicyclic α-amino acids bearing a (2-phenyl)benzoyl protective group to acrylonitrile under mild organic photoredox catalysis conditions furnished γ-amino acid derivatives with high retention of chirality via the memory of chirality (MOC) strategy. The retention of chirality in the photoinduced decarboxylation was strongly dependent on the structure of the alicyclic α-amino acids and alkenes. To the best of our knowledge, this is the first example of the decarboxylative intermolecular radical addition to alkenes with retention of chirality at the position of radical generation using the MOC strategy.
Reductive ipso-radical cyclization onto aromatic rings of five-membered alicyclic amino acids bearing N-(2-phenyl)benzoyl groups by photoinduced electron transfer promoted decarboxylation
Yamada, Tomoaki,Ozaki, Yui,Yamawaki, Mugen,Sugiura, Yoshihiko,Nishino, Kana,Morita, Toshio,Yoshimi, Yasuharu
, p. 835 - 838 (2017/02/18)
A new radical cyclization has been developed for the one-step synthesis of spiro dihydroisoquinolinone derivatives from alicyclic amino acids bearing N-(2-phenyl)benzoyl groups through photoinduced electron transfer (PET)-promoted decarboxylation. Reductive ipso-radical cyclization onto a benzene ring by an alkyl radical is achieved under mild conditions for the first time, although the substrates are limited to five-membered aliphatic carboxylic acids bearing N-(2-phenyl)benzoyl groups.
Indium-mediated alkynylation of sugars: Synthesis of C-glycosyl compounds bearing a protected amino alcohol moiety
Ayed, Charfedinne,Palmier, Sara,Lubin-Germain, Nadge,Uziel, Jacques,Augé, Jacques
scheme or table, p. 2566 - 2570 (2011/01/12)
The coupling of glycals with an alkynyl iodide bearing a protected amino alcohol moiety was achieved in the presence of metallic indium under Barbier conditions. It gave functionalized C-glycosyl compounds, precursors of C-glycosyl amino acids with α conf
Highly Enhanced Enantioselectivity in the Memory of Chirality via Acyliminium Ions
Wanyoike, G. Ng'ang'a,Onomura, Osamu,Maki, Toshihide,Matsumura, Yoshihiro
, p. 1875 - 1877 (2007/10/03)
(Matrix Presented) Electrochemical oxidation of N-acylated serine derivative 1b in methanol gave optically active methoxylated compound 2b with an enantiomeric excess of up to 80%. The bulky o-phenyl benzoyl N-protecting group was found to be the main con
