14212-54-5

Usage

Synthesis

A solution of 0.05 M Na2HPO4 (10.0 mL) was added to a 25-mL solution of undiluted commercial household bleach (Clorox). The pH of the resulting buffered solution (0.55 M in NaOCl) was adjusted to pH 11.3 by addition of a few drops of 1 M NaOH solution. This solution was cooled to 0 °C and then added at once to a 0 °C solution of the manganese catalyst (260 mg, 0.4 mmol) and cis-o-methylstyrene (1.18 g, 10 mmol) in 10 mL of CH2Cl2. The two-phase mixture was stirred at room temperature, and the reaction progress was monitored by TLC. After 3 h, 100 mL of hexane was added to the mixture and the brown organic phase was separated, washed twice with 100 mL of H2O and once with 100 mL of saturated NaCl solution, and then dried (Na2SO4). After solvent removal, the residue was purifified by flflash chromatography on silica gel to afford the epoxide (0.912 g, 68%). The ee of the epoxide was determined to be 84% by 1 H NMR analysis in the presence of Eu(hfc)3. Reference: Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296?2298.

Uses

Chiral building block. Tool for studying enzyme hydrolysis rates.

InChI:InChI=1/C9H10O/c1-7-9(10-7)8-5-3-2-4-6-8/h2-7,9H,1H3/t7-,9+/m1/s1

Upstream product

• 873-66-5 1-propenylbenzene 
• 108167-42-6 (-)-2-<(S)-N-(α-methylbenzyl)-N-benzylsulfamyl>-3-(pentafluorophenyl)oxaziridine 
• 766-90-5 cis-1-phenyl-1-propylene 
• 55380-59-1 ((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-trimethyl-ammonium; bromide 
• 14212-53-4 (1S,2R)-cis-methylstyrene oxide 
• 23355-97-7 1-phenylpropylene oxide 
• 104-94-9 4-methoxy-aniline 
• 95-20-5 2-methyl-1H-indole 
• 90-04-0 2-methoxy-phenylamine 
• 62-53-3 aniline 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 492-41-1 (1R,2S)-norephedrine 

Downstream Products

• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 104079-27-8 (1R,2S)-2-(2-hydroxyphenoxy)-1-phenylpropan-1-ol 
• 104079-28-9 (1S,2R)-1-(2-hydroxyphenoxy)-1-phenylpropan-1-ol 
• 1855-09-0 1-phenyl-1,2-propandiol 
• 135637-09-1 (1S,2R)-<1-2H>-1-phenylpropan-2-ol 
• 135637-10-4 (1S,2S)-<2-2H>-1-phenylpropan-1-ol 
• 14212-53-4 (1S,2R)-cis-methylstyrene oxide 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 5650-40-8 (R)-2-hydroxy-1-phenylpropan-1-one 
• 40560-98-3 (1S,2R)-1-phenylpropane-1,2-diol 
• 299-42-3 ephedrine 
• 676547-95-8 (1S,2R)-1-phenyl-1-(phenylseleno)propan-2-ol 

Relevant academic research and scientific papers

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Stereoselective radical-mediated cyclization of norephedrine derived o-bromobenzamides: Enantioselective synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolines

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Increasing the Activity and Efficiency of Stereoselective Oxidations by using Decoy Molecules in Combination with Rate-Enhancing Variants of P450Bm3

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Asymmetric alkene epoxidation with chromium oxo salen complexes. Effect of added phosphoryl ligands

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Any substituent at the 3,3'-positions is sufficient to give greater than 80% ee in the epoxidation of E-β-methylstyrene with chromium-salen complexes.

Isotope effects and the nature of enantioselectivity in the Shi epoxidation. The importance of asynchronicity

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Asymmetric epoxidation by chiral ketones derived from carbocyclic analogues of fructose

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N-Alkyl salts derived from ephedrine do not promote enantioselective Corey-Chaykovsky reactions involving sulfonium methylides under phase-transfer conditions

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High enantioselectivities in an (E)-alkene epoxidation by catalytically active chromium salen complexes. Insight into the catalytic cycle

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Amino acid-functionalized cyclopentadienyl molybdenum tricarbonyl complex and its use in catalytic olefin epoxidation

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