Stereoselective synthesis of enol acetates by the reaction of alkenylboronates with (diacetoxyiodo)benzene and sodium iodide

Murata, Miki; Satoh, Kaname; Watanabe, Shuichi; Masuda, Yoshio

doi:10.1039/a801469h

Cited by 25 publications

(5 citation statements)

References 13 publications

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“…This reaction (eq 56) stereoselectively affords products with inverted stereochemistry at the vinylic carbon. ( Z )-Alkenylboronates under these conditions give stereochemically pure ( E )-enol acetates in reasonable yields …”

Section: Oxidative Functionalization Of Alkenesmentioning

confidence: 94%

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Recent Developments in the Chemistry of Polyvalent Iodine Compounds

2002

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Section: Oxidative Functionalization Of Alkenesmentioning

confidence: 94%

“…(Z)-Alkenylboronates under these conditions give stereochemically pure (E)-enol acetates in reasonable yields. 148…”

Section: Oxidative Functionalization Of Alkenesmentioning

confidence: 99%

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

2002

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“…Two regioisomers emerge from Markovnikov or anti‐Markovnikov addition of which the latter also may give both double bond configurations (Scheme a). Although significant progress has been made, full control of regio‐ and stereochemistry can still be problematic . This hampers further functionalization of enol esters in which the stereochemical outcome depends on the double bond geometry (i. e. hydroformylation, hydrogenation).…”

Section: Methodsmentioning

confidence: 99%

Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

2018

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Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion.

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“…EAlkenylboronic acid 22a served as the suitable starting material. Following a procedure of Masuda et al, [66] the acid was converted in a highly selective manner to the Z-enol acetate 26. Cyclopropanation applying the Furukawa conditions [43±45] furnished the target compound 27 in 61% yield.…”

Section: Cyclopropanolsmentioning

confidence: 99%

Kinetic Enzymatic Resolution of Cyclopropane Derivatives

et al. 2003

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Abstract:The kinetic enzymatic resolution of various cyclopropane derivatives was systematically investigated. The study focused on synthetically useful cyclopropylmethanols (e.g., 18a/j or 19a/j) as well as some rarely investigated cyclopropanols (e.g., 24/25 or 27). The combination of enantioselective catalytic or diastereoselective synthesis of enantiomerically enriched compounds with enzymatic approaches ultimately led to the most convenient route to enantiomerically pure starting materials. Again, this was especially proven for the synthesis of cyclopropanols 18a/j and 19a/j. Key to the successful investigation was to rigorously establish an analytical tool for the analysis of enantiomeric composition of reaction mixtures.

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Stereoselective synthesis of enol acetates by the reaction of alkenylboronates with (diacetoxyiodo)benzene and sodium iodide

Cited by 25 publications

References 13 publications

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

Kinetic Enzymatic Resolution of Cyclopropane Derivatives

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