1611474-51-1Relevant articles and documents
Squaramide-Linked Chloramphenicol Base Hybrid Catalysts for the Asymmetric Michael Addition of 2,3-Dihydrobenzofuran-2-carboxylates to Nitroolefins
Yan, Linjie,Huang, Guanxin,Wang, Haifeng,Xiong, Fangjun,Peng, Haihui,Chen, Fener
, p. 99 - 103 (2018/01/17)
An array of hybrid catalysts incorporating a chloramphenicol base moiety linked to another chiral scaffold through a squaramide linker were developed and successfully used in the Michael addition of 2,3-dihydrobenzofuran-2-carboxylates to nitroolefins. Control experiments suggested that the hybrid catalysts were more reactive than nonhybridized bifunctional catalysts, and matching of the chirality between the two scaffolds was crucial for high reactivity and stereoselectivity. These hybrid organocatalysts could be used with a variety of substrates. At a 0.5 mol-% catalyst loading, a range of 2,3-dihydrobenzofuran-2-carboxylates derivatives bearing quaternary and tertiary stereogenic centers were obtained in high yields (up to 98 %) with excellent enantioselectivities (up to 99 % ee) and moderate diastereoselectivities (up to 8:92 dr).
Kinetic Resolution of 5-Substituted Oxazinones with Bifunctional Chiral Base/Squaramide Organocatalysts
Er?ksüz, Serap,Neud?rfl, J?rg M.,Berkessel, Albrecht
, p. 1278 - 1281 (2017/06/27)
5-Substituted oxazinones provide N-protected β 2 -amino acid esters upon alcoholytic ring opening. Thus far, this access to enantiopure β 2 -amino acids has been restricted to the use of enzymes (hydrolases) as catalysts for the kine
Syntheses and applications of (thio)urea-containing chiral quaternary ammonium salt catalysts
Novacek, Johanna,Waser, Mario
supporting information, p. 805 - 809 (2014/03/21)
We herein report our efforts to obtain a new class of systematically modified bifunctional (thio)urea-containing quaternary ammonium salts based on easily obtainable chiral backbones. Among the different classes of catalysts that were successfully synthes
Syntheses and Applications of (Thio)Urea-Containing Chiral Quaternary Ammonium Salt Catalysts
Novacek, Johanna,Waser, Mario
supporting information, p. 802 - 809 (2015/10/05)
We herein report our efforts to obtain a new class of systematically modified bifunctional (thio)urea-containing quaternary ammonium salts based on easily obtainable chiral backbones. Among the different classes of catalysts that were successfully synthesized, those based on trans-1,2-cyclohexane diamine were found to be the most powerful for the asymmetric α-fluorination of β-keto esters. Selectivities up to 93:7 could be obtained by using only 2 mol-% of the optimized catalyst. The importance of the bifunctional nature of these catalysts was demonstrated by control experiments using simplified monofunctional catalyst analogues, which gave almost racemic product only.