136137-85-4Relevant articles and documents
Diastereoselective ritter-like reaction on cyclic trifluoromethylated N,O-acetals derived from L-tartaric acid
Jamaa, Abdelkhalek Ben,Grellepois, Fabienne
, p. 10360 - 10375 (2018/05/31)
Despite the presence of the highly electron-withdrawing fluorinated substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal L-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product depend on the substituents on the hydroxyl groups of the tartaric acid scaffold. This methodology gave access to enantiopure, highly functionalized 5-(trifluoromethyl)pyrrolidin-2-one derivatives, bearing the fluorinated substituent on a tetrasubstituted carbon.
Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
, p. 1008 - 1016 (2015/08/18)
Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
Ultrasound-assisted addition of alcohols to N-acyliminium ions mediated by In(OTf)3 and synthesis of 1,2,3-triazoles
Stefani, Hélio A.,Ali, Bakhat,Ferreira, Fernando P.
, p. 3400 - 3405 (2014/06/09)
An easy and mild approach using ultrasound-assisted reaction addition of alcohols to N-acyliminium ion mediated by Lewis acid, In(OTf)3, allowed the synthesis of ether pyrrolidinones; next, the products were converted to 1,2,3-triazoles using c
The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3, 4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes
Serra, M. Elisa Silva,Murtinho, Dina,Goth, Albertino
, p. 315 - 319 (2013/04/24)
The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural l-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine.
Enantioselective trimethylsilylcyanation of benzaldehyde using pyrrolidine-based chiral salen ligands
Serra, M. Elisa Silva,Murtinho, Dina,Goth, Albertino
scheme or table, p. 64 - 69 (2010/08/07)
The in situ formed Ti(IV) complexes of several pyrrolidine-based chiral salen ligands derived from natural (L)-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of benzaldehyde. The catalysts were found to be very active, producing the corresponding product, O-trimethylsilylmandelonitrile, in high yields (>94%) and enantioselectivities of up to 88%.
Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic N-acyliminium ions: stereoselective synthesis of functionalized N-heterocycles
Vieira, Adriano S.,Ferreira, Fernando P.,Fiorante, Pedro F.,Guadagnin, Rafael C.,Stefani, Hélio A.
, p. 3306 - 3314 (2008/09/21)
The stereoselective nucleophilic addition of potassium aryl- and alkynyltrifluoroborates to cyclic N-acyliminium ion derivatives from N-benzyl-3,4,5-triacetoxy-2-pyrrolidinone, affording the respective 5-substituted 2-pyrrolidinone is described. The products were obtained in moderate to good yields and with preference for the syn diastereomer.
Practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate from L-tartaric acid
Tomori, Hiroshi,Maruyama, Hiroshi,Ogura, Katsuyuki
, p. 415 - 423 (2007/10/03)
An efficient method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate is described starting from L-tartaric acid, which affords the desired compounds with 99% ee in good overall yields (63-74%).
Chiral cyclic imides with c2-symmetry. Novel reagents for the synthesis of optically pure lactones containing three contiguous tertiary centers
Yoda, Hidemi,Shirakawa, Koji,Takabe, Kunihiko
, p. 3401 - 3404 (2007/10/02)
Asymmetric reactions employing C2-symmetrical imides readily prepared from L-tartaric acid with Grignard reagents and sodium borohydride afforded a separable mixture of two hydroxyamides with high diastereoselectivity. Products were lactonized
