24193-22-4Relevant academic research and scientific papers
Stereospecific isomerization of 3-substituted-3-bromo-1,2-epoxypropanes using magnesium bromide
Karikomi, Michinori,Takayama, Takeshi,Haga, Kazuo
, p. 4487 - 4490 (2002)
A novel stereospecific isomerization reaction of 3-substituted-3-bromo-1,2-epoxypropane derivatives into 1-substituted-3-bromo-1,2-epoxypropane derivatives is described. The choice of the solvent crucially influences the isomerization. The tendency of this isomerization could be predicted by comparison of the free energies calculation using ab initio and DFT methods.
Palladium-Promoted Neutral 1,4-Brook Rearrangement/Intramolecular Allylic Cyclization Cascade Reaction: A Strategy for the Construction of Vinyl Cyclobutanols
Zhang, Hao,Ma, Shiqiang,Yuan, Ziyun,Chen, Peng,Xie, Xingang,Wang, Xiaolei,She, Xuegong
supporting information, p. 3478 - 3481 (2017/07/15)
A cascade reaction to build vinyl cyclobutanol rings through activation of vinyl epoxides by palladium, followed by 1,4-Brook rearrangement and intramolecular cyclization with a palladium complex of the resulting carbon anion, is described. Through this cascade reaction, several highly substituted cyclobutanol substrates were achieved in good yields with high stereoselectivities.
Enantioselective bio-hydrolysis of various racemic and meso aromatic epoxides using the recombinant epoxide hydrolase Kau2
Zhao, Wei,Kotik, Michael,Iacazio, Gilles,Archelas, Alain
, p. 1895 - 1908 (2015/06/02)
Abstract Epoxide hydrolase Kau2 overexpressed in Escherichia coli RE3 has been tested with ten different racemic and meso α,β-disubstituted aromatic epoxides. Some of the tested substrates were bi-functional, and most of them are very useful building blocks in synthetic chemistry applications. As a general trend Kau2 proved to be an extremely enantioselective biocatalyst, the diol products and remaining epoxides of the bioconversions being obtained - with two exceptions - in nearly enantiomerically pure form. Furthermore, the reaction times were usually very short (around 1 h, except when stilbene oxides were used), and the use of organic co-solvents was well tolerated, enabling very high substrate concentrations (up to 75 g/L) to be reached. Even extremely sterically demanding epoxides such as cis- and trans-stilbene oxides were transformed on a reasonable time scale. All reactions were successfully conducted on a 1 g preparative scale, generating diol- and epoxide-based chiral synthons with very high enantiomeric excesses and isolated yields close to the theoretical maximum. Thus we have here demonstrated the usefulness and versatility of lyophilized Escherichia coli cells expressing Kau2 epoxide hydrolase as a highly enantioselective biocatalyst for accessing very valuable optically pure aromatic epoxides and diols through kinetic resolution of racemates or desymmetrization of meso epoxides.
Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation
Greszler, Stephen N.,Reichard, Holly A.,Micalizio, Glenn C.
supporting information; scheme or table, p. 2766 - 2774 (2012/03/22)
A convergent synthesis of highly substituted and stereodefined dihydroindanes is described from alkoxide-directed Ti-mediated cross-coupling of internal alkynes with substituted 4-hydroxy-1,6-enynes (substrates that derive from 2-directional functionaliza
Asymmetric aminolysis of aromatic epoxides: A facile catalytic enantioselective synthesis of anti-β-amino alcohols
Bartoli, Giuseppe,Bosco, Marcella,Carlone, Armando,Locatelli, Manuela,Massaccesi, Massimo,Melchiorre, Paolo,Sambri, Letizia
, p. 2173 - 2176 (2007/10/03)
The first asymmetric aminolysis of trans-aromatic epoxides with anilines is described. The process affords enantioenriched anti-β-amino alcohols in up to 99% ee. The complete regio- and diastereoselectivity observed uses commercially available [Cr(Salen)CI] as a Lewis acid catalyst and in combination with a very simple experimental procedure renders the present reaction a facile and practical tool for the synthesis of chiral nonracemic anti-β-amino alcohols.
Rearrangement Reactions of Epoxides in the Presence of 2-Mercaptopyridine N-Oxide Sodium Salt.
Lampard, Christopher,Murphy, John A.,Lewis, Norman
, p. 3841 - 3848 (2007/10/02)
Reaction of glycidyl bromides and tosylates with sodium salt of mercaptopyridine N-oxide led to the formation of episulphides.
A Novel Probe for Free Radicals featuring Epoxide Cleavage
Dickinson, Julia M.,Murphy, John A.,Patterson, Christopher W.,Wooster, Nicholas F.
, p. 1179 - 1184 (2007/10/02)
This paper describes the identification of carbon-carbon bond cleavage within a defined range of epoxides as being a reaction type which is specifically diagnostic of free radicals adjacent to the epoxide.The speed of the epoxide cleavage is greater than
