1362860-73-8Relevant academic research and scientific papers
Asymmetric Oxy-Michael Addition to γ-Hydroxy-α,β-Unsaturated Carbonyls Using Formaldehyde as an Oxygen-Centered Nucleophile
Yoneda, Naoki,Hotta, Ayano,Asano, Keisuke,Matsubara, Seijiro
supporting information, p. 6264 - 6266 (2015/02/19)
Formaldehyde was utilized as an oxygen-centered nucleophile in an asymmetric oxy-Michael addition to γ-hydroxy-α,β-unsaturated carbonyl compounds using bifunctional organocatalysts through hemiacetal intermediates. The cyclic acetal product could be further transformed into β-hydroxycarbonyl compounds, useful synthetic intermediates leading to various important target molecules. As such, this method is an example of a novel formal asymmetric hydration of α,β-unsaturated carbonyl compounds.
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
