3453-63-2Relevant articles and documents
Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B
Dussart, Nicolas,Trinh, Huu Vinh,Gueyrard, David
supporting information, p. 4790 - 4793 (2016/10/14)
The preparation of exo-enol esters from cyclic anhydrides is reported using a modified Julia olefination. The reaction is highly stereoselective. The Smiles rearrangement can be performed in a one-pot process, giving a straightforward access to exo-enol lactones. Furthermore, the reaction was extended to semistabilized sulfones, and this methodology was applied to the synthesis of maculalactone B.
One-pot synthesis of phthalides via regioselective intramolecular cyclization from ortho-alkynylbenzaldehydes
Li, Jim,Chin, Elbert,Lui, Alfred S.,Chen, Lijing
scheme or table, p. 5937 - 5939 (2010/11/21)
A one-pot synthesis of phthalides via an intramolecular 5-exo-dig cyclization of ortho-alkynylbenzaldehydes under mild NaClO2 oxidation conditions is described.
Catalytic activation of the leaving group in the SN2 reaction
Yamamoto, Hirofumi,Pandey, Ghanshyam,Asai, Yumiko,Nakano, Mayo,Kinoshita, Atsushi,Namba, Kosuke,Imagawa, Hiroshi,Nishizawa, Mugio
, p. 4029 - 4032 (2008/02/10)
A novel catalytic activation of the leaving group in the SN2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)2 to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives resulted in inversion of stereochemistry, which is a definitive feature of the S N2 reaction. The procedure is applicable for benzoazepine synthesis.
