Access the full text.
Sign up today, get DeepDyve free for 14 days.
A. Ward, J. Wolfe (2011)
Stereoselective synthesis of substituted 1,3-oxazolidines via Pd-catalyzed carboamination reactions of O-vinyl-1,2-amino alcohols.Organic letters, 13 17
A. Rao, S. Paknikar, J. Kirtane (1983)
Recent advances in the preparation and synthetic applications of oxiranesTetrahedron, 39
X.Eric Hu (2002)
Lewis acid promoted regio- and stereoselective hetero nucleophilic addition to a piperidinyl aziridine. Synthesis of trans 3-amino-4-substituted piperidinesTetrahedron Letters, 43
D. Hodgson, E. Kirton, S. Miles, S. Norsikian, N. Reynolds, S. Coote (2005)
Deprotonation-electrophile trapping of terminal epoxides.Organic & biomolecular chemistry, 3 10
Jack Scott, Robert Williams (2002)
Total synthesis of (-)-tetrazomine. Determination of the stereochemistry of tetrazomine and the synthesis and biological activity of tetrazomine analogues.Journal of the American Chemical Society, 124 12
Rosmara Mansueto, F. Perna, A. Salomone, S. Florio, V. Capriati (2013)
Dynamic resolution of lithiated ortho-trifluoromethyl styrene oxide and the effect of chiral diamines on the barrier to enantiomerisation.Chemical communications, 49 43
S. Gandhi, A. Bisai, B. Prasad, V. Singh (2007)
Studies on the Reaction of Aziridines with Nitriles and Carbonyls: Synthesis of Imidazolines and OxazolidinesJournal of Organic Chemistry, 72
Linliang Yu, Wei-cheng Zhou, Zhenyu Wang (2011)
Synthesis and in vitro antibacterial activity of oxazolidine LBM-415 analogs as peptide deformylase inhibitors.Bioorganic & medicinal chemistry letters, 21 5
A. Anderson, Jesse Blazek, Parie Garg, B. Payne, R. Mohan (2000)
Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketonesTetrahedron Letters, 41
B. Kang, Aaron Miller, S. Goyal, S. Nguyen (2009)
Sc(OTf)(3)-catalyzed condensation of 2-alkyl-N-tosylaziridine with aldehydes or ketones: an efficient synthesis of 5-alkyl-1,3-oxazolidines.Chemical communications, 26
J. Liebman, A. Greenberg (1976)
A survey of strained organic moleculesChemical Reviews, 76
A. Abbotto, V. Capriati, L. Degennaro, S. Florio, R. Luisi, M. Pierrot, A. Salomone (2001)
A stereospecific synthesis of oxazolinyloxiranes.The Journal of organic chemistry, 66 9
A. Sella, H. Basch, S. Hoz (1996)
Reactivity of Strained Compounds: Is Ground State Destabilization the Major Cause for Rate Enhancement?1Journal of the American Chemical Society, 118
Ioana Ungureanu, P. Klotz, A. Mann (2000)
Phenylaziridine als maskierte 1,3‐Dipole in Reaktionen mit nicht aktivierten AlkenenAngewandte Chemie, 112
F. Cordero, A. Brandi, C. Querci, A. Goti, F. Sarlo, A. Guarna (1990)
Rearrangement of isoxazoline-5-spiro derivatives. 5. Diastereofacial selectivity in the cycloaddition of substituted five-membered cyclic nitrones and methylenecyclopropanes. Stereoselective synthesis of 3,5-substituted indolizidinonesJournal of Organic Chemistry, 55
Akira Miyashita, Takeshi Shimada, Atsushi Sugawara, H. Nohira (1986)
Nickel-catalyzed ring-opening reactions of epoxides and their regioselectivities.Chemistry Letters, 15
Ya Du, Ying Wu, An‐Hua Liu, Liang‐Nian He (2008)
Quaternary ammonium bromide functionalized polyethylene glycol: a highly efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions.The Journal of organic chemistry, 73 12
J. Elings, H. Lempers, R. Sheldon (2000)
Solid-Acid Catalysed Rearrangement of Cyclic a,-Epoxy KetonesEuropean Journal of Organic Chemistry
M. Ghorai, Kalpataru Das, D. Shukla (2007)
Lewis acid-mediated highly regioselective SN2-Type ring-opening of 2-aryl-N-tosylazetidines and aziridines by alcohols.The Journal of organic chemistry, 72 15
L. Ferguson (1970)
Ring strain and reactivity of alicyclesJournal of Chemical Education, 47
Pandur Balaji, S. Chandrasekaran (2014)
Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion.Chemical communications, 50 1
Lawrence Pratt, Binh Mai, B. Ramachandran (2012)
Carbenoid alkene insertion reactions of oxiranyllithiums.The Journal of organic chemistry, 77 19
D. Hodgson, E. Gras (2002)
Recent Developments in the Chemistry of Lithiated EpoxidesChemInform, 33
Y. Fan, O. Kwon (2011)
Diversity-Oriented Synthesis Based on the DPPP-Catalyzed Mixed Double-Michael Reactions of Electron-Deficient Acetylenes and β-Amino AlcoholsMolecules, 16
R. Hadjadj-Aoul, A. Bouyacoub, F. Volatron (2014)
Reactivity of Di‐tert‐butyl‐oxiranyllithium – An Ab Initio StudyEuropean Journal of Organic Chemistry, 2014
A. Pandey, Asit Ghosh, Prabal Banerjee (2015)
Lewis‐Acid‐Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]‐Cycloaddition of Epoxides with Donor–Acceptor Cyclopropanes: Synthesis of Functionalized TetrahydrofuransEuropean Journal of Organic Chemistry, 2015
K. Williamson, T. Yoon (2010)
Iron-catalyzed aminohydroxylation of olefins.Journal of the American Chemical Society, 132 13
D. Hodgson, T. Buxton, I. Cameron, E. Gras, E. Kirton (2003)
Enantioselective synthesis of epoxides by alpha-deprotonation--electrophile trapping of achiral epoxides.Organic & biomolecular chemistry, 1 23
V. Sriramurthy, Gregg Barcan, O. Kwon (2007)
Bisphosphine-catalyzed mixed double-Michael reactions: asymmetric synthesis of oxazolidines, thiazolidines, and pyrrolidines.Journal of the American Chemical Society, 129 43
D. Michaelis, C. Shaffer, T. Yoon (2007)
Copper(II)-catalyzed aminohydroxylation of olefins.Journal of the American Chemical Society, 129 7
R. Luisi, V. Capriati, C. Carlucci, L. Degennaro, S. Florio (2003)
Lithiation of optically active oxazolinyloxiranes: configurational stabilityTetrahedron, 59
J. Smith (1984)
Synthetically Useful Reactions of EpoxidesSynthesis, 1984
Asit Ghosh, A. Pandey, Prabal Banerjee (2015)
Lewis Acid Catalyzed Annulation of Donor-Acceptor Cyclopropane and N-Tosylaziridinedicarboxylate: One-Step Synthesis of Functionalized 2H-Furo[2,3-c]pyrroles.The Journal of organic chemistry, 80 14
M. Ghorai, K. Ghosh, Kalpataru Das (2006)
Copper(II) triflate promoted cycloaddition of α-alkyl or aryl substituted N-tosylaziridines with nitriles: a highly efficient synthesis of substituted imidazolinesTetrahedron Letters, 47
Ryoko Maeda, R. Ishibashi, Ryo Kamaishi, Kensuke Hirotaki, H. Furuno, T. Hanamoto (2011)
AgSbF6-promoted cycloaddition reaction of 2-trifluoromethyl-N-tosylaziridine with aldehydes.Organic letters, 13 23
C. Wolf, Hanhui Xu (2011)
Asymmetric catalysis with chiral oxazolidine ligands.Chemical communications, 47 12
M. Ghorai, K. Ghosh (2007)
Lewis acid mediated nucleophilic ring opening followed by cycloaddition of 2-aryl-N-tosylaziridines with carbonyl compounds: further support towards an SN2-type mechanismTetrahedron Letters, 48
D. Hodgson, S. Norsikian (2001)
First Direct Deprotonation−Electrophile Trapping of Simple Epoxides: Synthesis of α,β-Epoxysilanes from Terminal EpoxidesOrganic Letters, 3
D. Hodgson, N. Reynolds, S. Coote (2004)
Substituted epoxides by lithiation of terminal epoxides.Organic letters, 6 23
R. Parker, N. Isaacs (1959)
Mechanisms Of Epoxide ReactionsChemical Reviews, 59
Dongxu Chen, Xiaoyi Chen, Taiping Du, Lichun Kong, R. Zhen, Shaocheng Zhen, Y. Wen, Gangguo Zhu (2010)
Highly efficient and diastereoselective synthesis of 1,3-oxazolidines featuring a palladium-catalyzed cyclization reaction of 2-butene-1,4-diol derivatives and iminesTetrahedron Letters, 51
Jiayun He, Jesse Ling, P. Chiu (2014)
Vinyl epoxides in organic synthesis.Chemical reviews, 114 16
J. Meinwald, S. Labana, M. Chadha (1963)
Peracid Reactions. III.1 The Oxidation of Bicyclo [2.2.1]heptadiene2Journal of the American Chemical Society, 85
D. Hodgson, E. Gras (2002)
Chiral epoxides by desymmetrizing deprotonation of meso-epoxides.Angewandte Chemie, 41 13
Benjamin Rotstein, S. Zaretsky, Vishal Rai, A. Yudin (2014)
Small heterocycles in multicomponent reactions.Chemical reviews, 114 16
Gert Callebaut, Tamara Meiresonne, N. Kimpe*, Sven Mangelinckx (2014)
Synthesis and reactivity of 2-(carboxymethyl)aziridine derivatives.Chemical reviews, 114 16
Luke Elliott, Joe Wrigglesworth, B. Cox, G. Lloyd‐Jones, K. Booker‐Milburn (2011)
2,2-Difunctionalization of alkenes via Pd(II)-catalyzed aza-Wacker reactions.Organic letters, 13 4
C. Huang, A. Doyle (2014)
The chemistry of transition metals with three-membered ring heterocycles.Chemical reviews, 114 16
G. Singh, M. D’hooghe, N. Kimpe* (2007)
Synthesis and reactivity of C-heteroatom-substituted aziridines.Chemical reviews, 107 5
I. Ungureanu, P. Klotz, A. Mann (2000)
Phenylaziridine as a Masked 1,3 Dipole in Reactions with Nonactivated Alkenes We thank Professor C. G. Wermuth for stimulating discussions.Angewandte Chemie, 39 24
D. Hodgson, Naeem Kaka (2008)
Asymmetric synthesis of alpha-alkylated aldehydes using terminal epoxide-derived chiral enamines.Angewandte Chemie, 47 51
D. Hodgson, C. Bray, N. Kindon (2004)
Enamines from terminal epoxides and hindered lithium amides.Journal of the American Chemical Society, 126 22
An efficient method for the synthesis of oxazolidine derivatives from aziridines and in situ generated aldehydes from Meinwald rearrangements of the epoxides has been developed. This method gives easy access to functionalized oxazolidines, which are constitutional moieties present in several natural products and biologically active molecules. The scope of the title transformation has also been elaborated with a variety of substrates.
Asian Journal of Organic Chemistry – Wiley
Published: Mar 1, 2016
Keywords: ; ; ; ;
Read and print from thousands of top scholarly journals.
Already have an account? Log in
Bookmark this article. You can see your Bookmarks on your DeepDyve Library.
To save an article, log in first, or sign up for a DeepDyve account if you don’t already have one.
Copy and paste the desired citation format or use the link below to download a file formatted for EndNote
Access the full text.
Sign up today, get DeepDyve free for 14 days.
All DeepDyve websites use cookies to improve your online experience. They were placed on your computer when you launched this website. You can change your cookie settings through your browser.