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• 108-05-4 vinyl acetate 
• 93-56-1 phenylethane 1,2-diol 
• 108-24-7 acetic anhydride 
• 2243-35-8 2-acetoxyacetophenone 
• 108-22-5 Isopropenyl acetate 
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• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 75-36-5 acetyl chloride 
• 244056-65-3 (2S,6S,7R,9S,14R)-14-Phenyl-2,9-bis(triisopropylsilyloxymethyl)-1,8,13,16-tetraoxadispiro<5.0.5.4>hexadecane 

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• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 

Relevant academic research and scientific papers

Structurally Defined α-Tetralol-Based Chiral Hypervalent Iodine Reagents

A novel class of chiral hypervalent iodine reagents containing an α-tetralol scaffold is introduced. Iodine triacetate is employed in a key step as a highly selective and efficient iodinating reagent for a short and convenient synthesis of iodine(III) derivatives. Solid-state X-ray analyses offer valuable structural information, while reactivities and stereoselectivities are investigated in three model reactions.

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Alternative Strategies with Iodine: Fast Access to Previously Inaccessible Iodine(III) Compounds

Non-iodinated arenes can be easily and selectively converted into (diacetoxyiodo)arenes in a single step under mild conditions by using iodine triacetates as reagents. The oxidative step is decoupled from the synthesis of hypervalent iodine(III) reagents, which can now be prepared conveniently in a one-pot synthesis for subsequent reactions without prior purification. The chemistry of iodine triacetates was also expanded to heteroatom ligand exchanges to form novel inorganic hypervalent iodine compounds.

Catalytic Asymmetric Diamination of Styrenes

An enantioselective catalytic vicinal diamination of styrenes is reported, which proceeds under entirely intermolecular reaction control. It relies on a chirally modified aryliodine(I) catalyst and proceeds within an iodine(I/III) manifold with conventional 3-chloroperbenzoic acid as a terminal oxidant. An environmentally benign solvent combination not only adds to the attractiveness of the process but also slows down the rate of the undesired background reaction. A total of 30 examples are presented, which consistently provide high enantiomeric excesses in the range 91-98%.

Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions

Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.

Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

A procedure for the intermolecular enantioselective dioxygenation of alkenes under iodine(III) catalysis has been developed. This protocol employs Selectfluor as the terminal oxidant together with a defined C 2-symmetric aryl iodide as the organocatalyst. This enantioselective reaction proceeds under mild conditions and converts a series of terminal and internal styrenes into the corresponding vicinal diacetoxylation products with up to 96% ee.

Enantioselective Prevost and Woodward reactions using chiral hypervalent iodine(iii): Switchover of stereochemical course of an optically active 1,3-dioxolan-2-yl cation

Optically active 1,3-dioxolan-2-yl cation intermediates were generated during enantioselective dioxyacetylation of alkene with chiral hypervalent iodine(III). Regioselective attack of a nucleophile toward the intermediate resulted in reversal of enantioselectivity of the dioxyacetylation. The Royal Society of Chemistry.

ZrCl4 as an efficient catalyst for a novel one-pot protection/deprotection synthetic methodology

(Chemical Equation Presented) A catalytic quantity of ZrCl4 (20 mol %) was found to be an efficient catalyst for the one-pot esterification and deprotection of (5S,6R)-5,6-diacetoxyoct-7-enoic acid in good yields (44-62%) with a lactone formed as a minor byproduct. ZrCl4 (10-20 mol %) was also sufficient to deprotect 1,3-dioxalane, bis-TBDMS ethers, and diacetate functional groups in excellent yields of up to 93%. ZrCl4 (1-10 mol %) also promoted diol protection as the acetonide in 90% yield and acted as a trans-esterification catalyst for a range of esters.

Chemoenzymatic synthesis of enantiomerically pure terminal 1,2-diols

A new practical method for the enzymatic synthesis of 1,2-diols has been developed by employing a lipase catalyzed one-pot transesterification protocol. A series of substituted α-acetoxyphenylethanones 3a-g have been reduced to the corresponding alcohols under mild conditions employing sodium borohydride and moist neutral alumina, and further subjected for lipase catalyzed irreversible transesterification in the same pot to give mono- and diacetate diols (R)-4 and (S)-5, which on hydrolysis afforded terminal 1,2-diols, (R)- and (S)-6 in high enantiomeric excess.

Dispiroketals in synthesis. Part 24. Preparation and use of chiral 2,2′-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s as new protecting and resolving agents for 1,2-diols

C2 symmetric chiral 2,2′-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s (S,S)-1 and (R,R)-1 were prepared from the corresponding glycidols and selectively reacted with 1,2-diols to give dispiroketals. The products of these reactions could be deprotected following treatment with fluoride, oxidation and reductive cleavage with samarium(II) iodide.