Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 2.

Akiba, Toshifumi; Tamura, Osamu; Hashimoto, Minoru; Kobayashi, Yuko; Katoh, Tadashi; Nakatani, Kazuhiko; Kamada, Masahiro; Hayakawa, Isao; Terashima, Shiro

doi:10.1016/s0040-4020(01)89666-6

Cited by 38 publications

(12 citation statements)

References 11 publications

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“…15 [α] D 20 = −8.9 °(c = 0.699, MeOH), lit. 16 4 the optical purity of (R,S)-2•TsOH prepared here was determined to be >99% ee by HPLC analysis of its 3,5-dinitrobenzamide. The analysis conditions for HPLC: chiral Synthesis of (S,R)-2•TsOH.…”

Section: H Nmrmentioning

confidence: 89%

Stereoselective Synthesis of cis-2-Fluorocyclopropanecarboxylic Acid

Shibue¹,

Fukuda²

2014

J. Org. Chem.

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Section: H Nmrmentioning

confidence: 89%

Stereoselective Synthesis of cis-2-Fluorocyclopropanecarboxylic Acid

Shibue¹,

Fukuda²

2014

J. Org. Chem.

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“…(4 R ,5 S )-Diphenyl-3-(3-phenyl-2-( E )-propenoyl)-2-oxazolidinone, 3c. 3c was prepared in 93% yield from (4 R ,5 S )-Diphenyl-2-oxazolidinone by following the same procedure as that used for 2b . mp: 271−274 °C.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Total Synthesis of (+)-Tolterodine, a New Muscarinic Receptor Antagonist, via Copper-Assisted Asymmetric Conjugate Addition of Aryl Grignard Reagents to 3-Phenyl-prop-2-enoyl-oxazolidinones

1998

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“…The title compound was prepared according to the literature procedure 20 for the synthesis of analogous 3-(2-bromopropionyl)-2-oxazolidinones. To a solution of (4 R ,5 S )-4,5-diphenyl-2-oxazolidinone (4.79 g, 20.0 mmol) in THF (130 mL) was added 1.59 M n -BuLi in hexane (13.2 mL, 21.0 mmol) at 0 °C. After being stirred for 15 min, the solution was treated with 2-bromopropionyl bromide (2.1 mL, 20.0 mmol) at 0 °C, and the mixture was stirred for 1 h at this temperature.…”

Section: Methodsmentioning

confidence: 99%

An Activated Germanium Metal-Promoted, Highly Diastereoselective Reformatsky Reaction

et al. 1998

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Activated germanium metal, prepared by the reduction of germanium(II) iodide with potassium metal, was found to promote the Reformatsky reaction effectively under mild conditions. In the presence of activated germanium metal, the reactions of alpha-bromo ketones 2a and 2b and alpha-bromo imides 2e and 2f with benzaldehyde (1a) proceeded smoothly to give the corresponding beta-hydroxy carbonyl compounds 3a, 3b, 3e and 3f, respectively, in good yields and with good syn diastereoselectivity. The activated germanium metal-promoted, asymmetric Reformatsky reaction of enantiomerically pure-oxazolidinone derivatives 2g-j with various aldehydes 1a-d was also examined; the highest diastereoselectivity was achieved when (1S,2R)-2-amino-1,2-diphenylethanol-derived 2j was used as the Reformatsky donor. The excellent diastereoselectivity could be explained in terms of the formation of a chairlike, six-membered transition state between the aldehyde and enolate as in the Zimmerman-Traxler model. A single recrystallization of the Reformatsky adducts, followed by hydrolysis and subsequent esterification, led to enantiomerically pure methyl 3-hydroxy-2-methylalkanoates 10j-m, with almost quantitative recovery of the enantiomerically pure 2-oxazolidinone 14.

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Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 2.

Cited by 38 publications

References 11 publications

Stereoselective Synthesis of cis-2-Fluorocyclopropanecarboxylic Acid

Stereoselective Synthesis of cis-2-Fluorocyclopropanecarboxylic Acid

Asymmetric Total Synthesis of (+)-Tolterodine, a New Muscarinic Receptor Antagonist, via Copper-Assisted Asymmetric Conjugate Addition of Aryl Grignard Reagents to 3-Phenyl-prop-2-enoyl-oxazolidinones

An Activated Germanium Metal-Promoted, Highly Diastereoselective Reformatsky Reaction

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