692730-97-5Relevant academic research and scientific papers
Convenient synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist
Ezawa, Tetsuya,Kawashima, Yuya,Noguchi, Takuya,Jung, Seunghee,Imai, Nobuyuki
, p. 266 - 281 (2017/02/18)
We have achieved a convenient enantioselective synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist in 19–40% overall chemical yields from the corresponding 2-arylbut-2-ene-1,4-diols with moderate to excellent asymmetric yields via regioselective acetylation using porcine pancreas lipase, catalytic enantioselective Simmons-Smith reactions, and amidation in aqueous organic solvent. This synthetic route is more efficient and less expensive than conventional methods.
Convenient synthesis of (+)-cis-4-(N-adamantyl-N-methylamino)-2,3-methano-2-phenylbutan-1-ol as a candidate of anti-Alzheimer's medicine via catalytic enantioselective Simmons-Smith reaction using l-phenylalanine-derived disulfonamide
Kawashima, Yuya,Ezawa, Tetsuya,Yamamura, Mai,Harada, Taisuke,Noguchi, Takuya,Imai, Nobuyuki
, p. 668 - 671 (2016/01/26)
The catalytic enantioselective Simmons-Smith reaction of (Z)-4-tert-butyldiphenylsiloxy-3-phenylbut-2-en-1-ol using l-phenylalanine-derived disulfonamide afforded (+)-cis-4-tert-butyldiphenylsiloxy-2,3-methano-3-phenylbutan-1-ol in quantitative yield with 71% ee. The 2,3-methano-3-phenylbutan-1-ol was easily converted to the corresponding 2,3-methano-3-phenylbutanoic acid, followed by amidation of the carboxylic acid with 1-adamantanamine sulfate in aqueous organic solvent to afford the corresponding 2,3-methano-3-phenylbutanamide in excellent yields. Convenient enantioselective synthesis of (+)-cis-4-(N-adamantyl-N-methylamino)-2,3-methano-2-phenylbutan-1-ol ((+)-AMMP) was achieved in 35% overall yield from the starting 1,4-diol via our developed key reactions.
Asymmetric syntheses of pharmaceuticals containing a cyclopropane moiety using catalytic asymmetric Simmons-Smith reactions of allylalcohols: Syntheses of optically active tranylcypromine and milnacipran
Ishizuka, Yuki,Fujimori, Hirohisa,Noguchi, Takuya,Kawasaki, Masashi,Kishida, Mari,Nagai, Takuya,Imai, Nobuyuki,Kirihara, Masayuki
, p. 1311 - 1313 (2013/10/22)
Asymmetric synthesis of tranylcypromine was achieved using an enantioselective Simmons-Smith cyclopropanation catalyzed by a simple disulfonamide derived from an -amino acid. The optically active milnacipran was also synthesized by porcine pancreas lipase-catalyzed selective monoacylation of the C4-hydroxy group in (Z)-2-phenylbut-2-ene-1,4-diol and the enantioselective Simmons-Smith cyclopropanation as the key steps.
On the regioselectivity of Pd-catalyzed additions of organoboronic acids to unsymmetrical alkynes
Kim, Nakjoon,Kim, Ki Seong,Gupta, Aruna Kumar,Oh, Chang Ho
, p. 618 - 619 (2007/10/03)
The Pd-catalyzed reaction of unsymmetrical alkynes 1 with organoboronic acids 2 gave a mixture of products 3 and 4, whose ratios were controlled by the electronic as well as steric effects of the substrates 1.
