180963-90-0Relevant academic research and scientific papers
Stereoselective Construction of Copaborneol and Longiborneol Frameworks by Intramolecular Double Michael Reaction
Ihara, Masataka,Makita, Kei,Fujiwara, Yuki,Tokunaga, Yuji,Facumoto, Keiichiro
, p. 6416 - 6421 (1996)
Stetreoselective synthesis of tricyclo3,8>decane 22 and tricyclo3,9>undecane 26 the basic skeleton of copaborneol and longiborneol, were achieved by the intramolecular double Michael reactions of 2-cyclopenten-1-ones 15-17.The substrates were prepared starting with tricyclo2,6>deca-4,8-dien-3-one (6).The intramolecular double Michael reactions were carried out under three different conditions: TMSCl-Et3N-ZnCl2.TMSI-(TMS)2NH, and Bu2BOTf-(TMS)2NH.The framework 26 of longiborneol was constructed in good yield using the latter two reagent systems.
Syntheses of α,β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides
Hon, Yung-Son,Lu, Ling,Chang, Rong-Chi,Lin, Sheng-Wun,Sun, Pei-Pei,Lee, Chia-Fu
, p. 9269 - 9279 (2007/10/03)
Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-αβ-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-αβ-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed. (C) 2000 Elsevier Science Ltd.
