2007
DOI: 10.1016/j.tetlet.2006.12.011
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Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide

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Cited by 31 publications
(19 citation statements)
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“…CuI (0.171 g, 0.898 mmol) was added under the flow of N 2 . The reaction temperature was raised to À50 8C, 3 [3] (0.811 g, 4.55 mmol) in dry THF (0.4 mL) was added to the reaction mixture and stirred for 3 h. After the mixture had been warmed to room temperature, a saturated aqueous solution of NH 4 Cl (10 mL) was added to the dark-colored mixture reaction. The mixture was diluted with EtOAc, and then the combined organic layer was washed with brine, dried over Na 2 SO 4 and concentrated in vacuo.…”
Section: Methodsmentioning
confidence: 99%
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“…CuI (0.171 g, 0.898 mmol) was added under the flow of N 2 . The reaction temperature was raised to À50 8C, 3 [3] (0.811 g, 4.55 mmol) in dry THF (0.4 mL) was added to the reaction mixture and stirred for 3 h. After the mixture had been warmed to room temperature, a saturated aqueous solution of NH 4 Cl (10 mL) was added to the dark-colored mixture reaction. The mixture was diluted with EtOAc, and then the combined organic layer was washed with brine, dried over Na 2 SO 4 and concentrated in vacuo.…”
Section: Methodsmentioning
confidence: 99%
“…[3] This was treated with vinylmagnesium chloride in THF in the presence of CuI to give (R)-4a in almost a quantitative yield. Next, the benzyl protective group in 4a was selectively removed, by treatment with lithiumethylenediamine-THF, [4] a modified Benkeser reduction.…”
Section: Carbon-chain Elongation and The Functional Group Transformatmentioning
confidence: 99%
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“…Enantiopure epoxides and diols are chiral intermediates or building blocks, which can be used for the synthesis of biologically active compounds such as antibi otics [4], antifungal drugs [5], antiandrogens [6], receptor agonists and antagonists [7][8][9], 11-heterosteroids [10], HIV protease inhibitors [11,12], nonsteroidal antiinflammatory drugs [13,14], and other natural products [15][16][17][18][19]. An EH-triggered cascade reaction enabled the asymmetric synthesis of two antitumor agents, which occur naturally in Panax ginseng [20].…”
Section: Introductionmentioning
confidence: 99%