10387-93-6Relevant articles and documents
Diastereoselective One-Pot Synthesis of Oxazolines Using Sulfur Ylides and Acyl Imines
Mehedi, Md Shafaat Al,Tepe, Jetze J.
supporting information, p. 7219 - 7226 (2019/06/14)
This work describes an extended version of the Corey-Chaykovsky reaction to access oxazolines using sulfur ylides and stable precursors of acyl imines. The reaction proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxazolines following in situ Heine-type aziridine ring expansion upon treatment with BF3·OEt2. Following the same one-pot procedure, amidine imides react with the sulfur ylides to provide imidazolines.
Catalytic syntheses of γ-functionalized α-keto esters from thioacetals and N,O-acetals
Krebs, Anke,Bolm, Carsten
scheme or table, p. 4055 - 4060 (2011/06/24)
Ethyl 2-(trimethylsilyloxy)acrylic ester (1a) reacts with thioacetals providing the corresponding α-keto-γ-thio esters in good to satisfactory yields. Whereas aminals do not react, N,O-acetals lead to γ-amino-α-keto esters in good to excellent yields. All reactions proceed under mild reaction conditions, and no additional work up is required. Subsequent transformations of the obtained products to the corresponding α-oximes have been demonstrated.
Asymmetric Sulfur Ylide Mediated Aziridination: Application in the Synthesis of the Side Chain of Taxol
Aggarwal, Varinder K.,Vasse, Jean-Luc
, p. 3987 - 3990 (2007/10/03)
(Formula presented). Sulfur ylide methodology has been used to construct the Taxol side chain with a high degree of enantioselectivity via a trans-aziridine followed by stereospecific rearrangement of the trans-benzoylaziridine into a trans-oxazoline.