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Your search keyword '"Hirohisa Fujimori"' showing total 3 results
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3 results on '"Hirohisa Fujimori"'

1. Convenient preparation of optically active cibenzoline and analogues from 3,3-diaryl-2-propen-1-ols

Author

Naka Koyata, Takuya Noguchi, Tsuyoshi Miura, Hirohisa Fujimori, Nobuyuki Imai, Hisashi Sasaki, Takuya Nagai, Rie Sato, Masayuki Kirihara, and Yoko Akaiwa

Subjects
Chemistry, Cyclopropanation, Organic Chemistry, Recrystallization (metallurgy), Ethylenediamine, Optically active, Medicinal chemistry, Chloride, Catalysis, Inorganic Chemistry, Hydrolysis, chemistry.chemical_compound, Cibenzoline, medicine, Organic chemistry, Physical and Theoretical Chemistry, medicine.drug
Abstract

( R )-(+)-Cibenzoline (95% ee) was synthesized in two steps from (+)-2,2-diphenylcyclopropylmethanol 3a (98% ee), which was oxidized with IBX in DMSO, followed by treatment with ethylenediamine in the presence of I 2 and K 2 CO 3 in t BuOH. Compound ( R )-(+)- 3a (98% ee) was prepared by cyclopropanation of 3,3-diphenyl-2-propen-1-ol 1 with Et 2 Zn and CH 2 I 2 in the presence of a catalytic amount of ( S )-2-(methanesulfonyl)amino-1-( p -toluenesulfonyl)amino-3-phenylpropane 2 , followed by esterification with 3,5-dinitorobenzoyl chloride, recrystallization, and hydrolysis.

Published
2009
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2. Asymmetric Syntheses of Pharmaceuticals Containing a Cyclopropane Moiety Using Catalytic Asymmetric Simmons–Smith Reactions of Allylalcohols: Syntheses of Optically Active Tranylcypromine and Milnacipran

Author

Mari Kishida, Takuya Nagai, Takuya Noguchi, Masashi Kawasaki, Masayuki Kirihara, Hirohisa Fujimori, Yuki Ishizuka, and Nobuyuki Imai

Subjects
Cyclopropanation, Stereochemistry, Tranylcypromine, Enantioselective synthesis, General Chemistry, Optically active, Catalysis, Cyclopropane, chemistry.chemical_compound, chemistry, medicine, Organic chemistry, Moiety, medicine.drug
Abstract

Asymmetric synthesis of tranylcypromine was achieved using an enantioselective Simmons–Smith cyclopropanation catalyzed by a simple disulfonamide derived from an α-amino acid. The optically active ...

Published
2013
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3. Asymmetric Syntheses of Pharmaceuticals Containing a Cyclopropane Moiety Using Catalytic Asymmetric Simmons-Smith Reactions of Allylalcohols: Syntheses of Optically Active Tranylcypromine and Milnacipran.

Author

Yuki Ishizuka, Hirohisa Fujimori, Takuya Noguchi, Masashi Kawasaki, Mari Kishida, Takuya Nagai, Nobuyuki Imai, and Masayuki Kirihara

Abstract

Asymmetric synthesis of tranylcypromine was achieved using an enantioselective SimmonsSmith cyclopropanation catalyzed by a simple disulfonamide derived from an α-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. [ABSTRACT FROM AUTHOR]

Published
2013
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