77924-52-8Relevant academic research and scientific papers
Regio- and Stereo-selective Ring Opening of Epoxides with Amide Cuprate Reagents
Yamamoto, Yoshinori,Asao, Naoki,Meguro, Masaki,Tsukada, Naofumi,Nemoto, Hisao,et al.
, p. 1201 - 1203 (1993)
Amide cuprate reagents attack the less hindered carbon atom of epoxides to give 1,2-amino alcohols in good yields; this procedure is applied to the synthesis of an aziridine alcohol bearing a carborane framework which is a potentially useful 10B carrier for boron neutron capture therapy.
Dual Activation of Unsaturated Amides with Schwartz's Reagent: A Diastereoselective Access to Cyclopentanols and N,O-Dimethylcyclopentylhydroxylamines.
Coelho, Aurélien,Souvenir Zafindrajaona, Mahasoa-Salina,Vallée, Alexis,Behr, Jean-Bernard,Vasse, Jean-Luc
supporting information, (2021/12/06)
The diastereoselective access to cyclopentanols and N,O-dimethylcyclopentylhydroxylamines from 4-pentenoic acid-derived Weinreb amides is described. Based on the concomitant generation of both the nucleophilic and the electrophilic poles by hydrozirconati
Hydrogen Bonding Phase-Transfer Catalysis with Potassium Fluoride: Enantioselective Synthesis of β-Fluoroamines
Pupo, Gabriele,Vicini, Anna Chiara,Ascough, David M. H.,Ibba, Francesco,Christensen, Kirsten E.,Thompson, Amber L.,Brown, John M.,Paton, Robert S.,Gouverneur, Véronique
supporting information, p. 2878 - 2883 (2019/02/14)
Potassium fluoride (KF) is an ideal reagent for fluorination because it is safe, easy to handle and low-cost. However, poor solubility in organic solvents coupled with limited strategies to control its reactivity has discouraged its use for asymmetric C-F
An improved chemoenzymatic synthesis of both enantiomers of trans-cyclopentane-1,2-diamine
Pena, Carmen,Gonzalez-Sabin, Javier,Rebolledo, Francisca,Gotor, Vicente
, p. 751 - 755 (2008/09/20)
An improved chemoenzymatic protocol for the synthesis of both enantiomers of trans-cyclopentane-1,2-diamine is described. The key part of the strategy relies on the synthesis and subsequent enzymatic resolution of its racemic precursor trans-N,N-diallylcy
Ytterbium Triflate and High Pressure-mediated Ring Opening of Epoxides with Amines
Meguro, Masaki,Asao, Naoki,Yamamoto, Yoshinori
, p. 2597 - 2602 (2007/10/02)
Ring opening of epoxides with amines in THF takes place very readily in the presence of catalytic amounts of ytterbium triflate to give the corresponding β-amino alcohols in good to high yields.With tri- and tetra-substituted epoxides, the use of an excess (2 - 3 equiv.) of the amine is needed.The Yb(OTf)3-catalysed reaction of epoxides with amines in CH2Cl2 is quite complex; the yield of amino alcohols is generally lower and depends upon the addition order of the catalyst, amine and epoxide.The ring opening is accomplished also under high pressures in the absence of Yb(OTf)3.Ring opening with a combination of Yb(OTf)3 in CH2Cl2 and high pressure is more effective than the use, independently, of either Yb(OTf)3 or the high-pressure method.Oxetanes and β-lactones undergo ring opening in the presence of Yb(OTf)3.
FACILE AMINOLYSIS OF EPOXIDES WITH DIETHYLALUMINUM AMIDES
Overman, Larry E.,Flippin, Lee A.
, p. 195 - 198 (2007/10/02)
Treatment of an epoxide with a diethylaluminum amide in dichloromethane at room temperature affords the corresponding β-amino alcohol in good yield.
