American Chemical Society (ACS)
Organic Letters
,  том 11 ,  издание 11 ,  страницы 2437-2440

Anti-Selective Epoxidation of Methyl α-Methylene-β-tert-butyldimethylsilyloxycarboxylate Esters. Evidence for Stereospecific Oxygen Atom Transfer in a Nucleophilic Epoxidation Process

Тип публикации: Journal Article
Дата публикации: 2009-04-27
American Chemical Society (ACS)
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
Methyl alpha-methylene-beta-tert-butyldimethylsilyloxycarboxylate esters are found to undergo diastereoselective epoxidation in the presence of potassium tert-butoxide-tert-butyl hydroperoxide to form anti products. In an effort to better understand mechanistic details of the transformation and the basis of diastereoselectivities observed, we studied the epoxidation of substrates with alpha-methylene groups containing (trans) deuterium labels and discovered that oxygen-atom transfer proceeds with > or = 95% stereospecificity in all cases examined. These and other experiments suggest that the mechanism of epoxidation is not distinguishable from a concerted process.
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Švenda J., Myers A. T. Anti-Selective Epoxidation of Methyl α-Methylene-β-tert-butyldimethylsilyloxycarboxylate Esters. Evidence for Stereospecific Oxygen Atom Transfer in a Nucleophilic Epoxidation Process // Organic Letters. 2009. Vol. 11. No. 11. pp. 2437-2440.
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Švenda J., Myers A. T. Anti-Selective Epoxidation of Methyl α-Methylene-β-tert-butyldimethylsilyloxycarboxylate Esters. Evidence for Stereospecific Oxygen Atom Transfer in a Nucleophilic Epoxidation Process // Organic Letters. 2009. Vol. 11. No. 11. pp. 2437-2440.
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TY - JOUR
DO - 10.1021/ol900665a
UR - https://doi.org/10.1021/ol900665a
TI - Anti-Selective Epoxidation of Methyl α-Methylene-β-tert-butyldimethylsilyloxycarboxylate Esters. Evidence for Stereospecific Oxygen Atom Transfer in a Nucleophilic Epoxidation Process
T2 - Organic Letters
AU - Švenda, Jakub
AU - Myers, Andrew T.
PY - 2009
DA - 2009/04/27
PB - American Chemical Society (ACS)
SP - 2437-2440
IS - 11
VL - 11
PMID - 19397300
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2009_Švenda,
author = {Jakub Švenda and Andrew T. Myers},
title = {Anti-Selective Epoxidation of Methyl α-Methylene-β-tert-butyldimethylsilyloxycarboxylate Esters. Evidence for Stereospecific Oxygen Atom Transfer in a Nucleophilic Epoxidation Process},
journal = {Organic Letters},
year = {2009},
volume = {11},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/ol900665a},
number = {11},
pages = {2437--2440},
doi = {10.1021/ol900665a}
}
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Švenda, Jakub, and Andrew T. Myers. “Anti-Selective Epoxidation of Methyl α-Methylene-β-tert-butyldimethylsilyloxycarboxylate Esters. Evidence for Stereospecific Oxygen Atom Transfer in a Nucleophilic Epoxidation Process.” Organic Letters, vol. 11, no. 11, Apr. 2009, pp. 2437-2440. https://doi.org/10.1021/ol900665a.