159974-69-3Relevant academic research and scientific papers
Chiral epoxides as a source of chiral β-oxidofunctionalised organolithium compounds: Reaction with electrophiles
Bachki, Abderrazak,Foubelo, Francisco,Yus, Miguel
, p. 2997 - 3008 (1996)
The reductive opening of chiral epoxides 1, 4, 7 and 11 with lithium powder and a catalytic amount of DTBB (5 mol %) in THF at -78°C, followed by treatment with different electrophiles [Bu(t)CHO, PhCHO, (CH2)5CO, PhCOMe, CO2/su
Asymmetric cycloetherifications by bifunctional aminothiourea catalysts: The importance of hydrogen bonding
Fukata, Yukihiro,Miyaji, Ryota,Okamura, Takaaki,Asano, Keisuke,Matsubara, Seijiro
, p. 1627 - 1634 (2013/07/27)
Chiral oxacyclic frameworks are prevalent in many natural products and bioactive compounds. In addition, a number of them are important synthetic intermediates. Thus, the synthesis of such structures is a significant goal in the field of organic chemistry. However, the development of catalytic asymmetric cycloetherification for the straightforward synthesis of these compounds remains a challenge. In this study, we propose the use of aminothiourea catalysis as an effective way to accomplish such a challenge. The asymmetric synthesis of chiral oxygen heterocycles, including tetrahydrofurans, tetrahydropyrans, and 1,3-dioxolanes, is demonstrated herein using intramolecular oxy-Michael addition mediated by bifunctional aminothiourea catalysts. Georg Thieme Verlag Stuttgart · New York.
Asymmetric synthesis of 1,3-dioxolanes by organocatalytic formal [3 + 2] cycloaddition via hemiacetal intermediates
Asano, Keisuke,Matsubara, Seijiro
supporting information; experimental part, p. 1620 - 1623 (2012/06/05)
A novel asymmetric formal [3 + 2] cycloaddition reaction for the synthesis of 1,3-dioxolanes using cinchona-alkaloid-thiourea-based bifunctional organocatalysts is reported. The reaction proceeds via the formation of hemiacetal intermediates between γ-hyd
Synthesis of a bifunctional 2,4-dihydroxy five-carbon synthon. Enantiomerically pure Δ2-isoxazolines by chromatographic resolution
Ticozzi, Calimero,Zanarotti, Antonio
, p. 7421 - 7424 (2007/10/02)
Chromatography on cellulose triacetate allows the separation of (R)- and (S)-4,5-dihydro-3-phenyl-5-isoxazolemethanol in 100% ee. Reductive ring cleavage, diastereoselective reduction of the 3-hydroxy ketones thus obtained, and oxidation of the phenyl rin
