880175-74-6Relevant academic research and scientific papers
Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis
Aggarwal, Varinder K.,Charmant, Jonathan P. H.,Fuentes, Daniel,Harvey, Jeremy N.,Hynd, George,Ohara, Diasuke,Picoul, Willy,Robiette, Raphael,Smith, Catherine,Vasse, Jean-Luc,Winn, Caroline L.
, p. 2105 - 2114 (2007/10/03)
The reactions of a range of amide-stabilized sulfur ylides derived from readily available camphor-derived sulfonium salts for the synthesis of glycidic amides have been studied. Primary, secondary, and tertiary amides were tested, and it was found that th
Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors
Matsunaga, Shigeki,Qin, Hongbo,Sugita, Mari,Okada, Shigemitsu,Kinoshita, Tomofumi,Yamagiwa, Noriyuki,Shibasaki, Masakatsu
, p. 6630 - 6639 (2007/10/03)
Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors is described. A Sm(O-i-Pr)3/(R)-H8-BINOL complex promoted the epoxidation reaction to afford products in high yield (up to quant) and high enantiomeric excess (up to >99.5% ee). Reaction proceeded smoothly using cumene hydroperoxide (CMHP) with low explosive hazard, and completed within 0.2-0.5 h with 5 mol % catalyst. Catalyst loading was successfully reduced to as little as 0.02 mol %. The N-acylpyrrole properties as well as efficient synthesis of α,β-unsaturated N-acylpyrroles are also described.
