10293-98-8Relevant articles and documents
Intramolecular cyclopropanation of epichlorohydrin-derived unsaturated chlorohydrins
Hodgson, David M.,Chung, Ying Kit,Paris, Jean-Marc
, p. 2264 - 2266 (2005)
Concise stereoselective syntheses of bicyclo[3.1.0]hexan-2-ols and a bicyclo[4.1.0]heptan-2-ol are achieved via regioselective ring-opening of epichlorohydrin with allylic and homoallylic Grignard reagents, followed by lithium 2,2,6,6-tetramethylpiperidide-induced intramolecular cyclopropanation of the resulting unsaturated chlorohydrins. Georg Thieme Verlag Stuttgart.
A novel gallium/samarium-mediated coupling of epoxides with allyl halides in aqueous media and synthesis of homoallylic alcohols
Gohain, Mukut,Prajapati, Dipak
, p. 90 - 91 (2005)
A mild and efficient protocol for the coupling of various substituted epoxides 1 with allylgallium reagent generated in situ in a Bu 4NBr-DMF-H2O system have been developed. The coupling is also found to be equally effective when samarium is used in lieu of gallium and the corresponding homoallylic alcohols 2 were obtained in almost comparable yields. Copyright
Lewis Acid Promoted Ring-Opening Allylation of Epichlorohydrin with Allylic Silanes and Stannanes To Afford 1-Chloro-5-alken-2-ols. A Short Synthesis of (S)-(-)-Ipsenol
Imai, Toshiro,Nishida, Shinya
, p. 4849 - 4852 (1990)
Epichlorohydrine (1) was allylated in good yields with representative allylic silanes (2, 5, 7, 9) and stannanes (12, 18) in the presence of appropriate Lewis acids.The reaction proceeds with ring opening at the unsubstituted site in 1 and with allylic inversion in the allylating agents to give 1-chloro-5-alken-2-ols cleanly.A short synthesis of (S)-(-)-ipsenol (29) from 1 and an (allenylmethyl)silane (26) demonstrates the utility of this method in organic synthesis.
An easy procedure for the highly regioselective conversion of epoxides to halohydrins
Bonini,Giuliano,Righi,Rossi
, p. 1863 - 1870 (2007/10/02)
Several epoxides and epoxy alcohols have been opened to the corresponding halohydrins by lithium halides with Amberlyst in CH3CN at room temperature: the reaction proceeds in quantitative yields with high degree of regioselectivity.
Chemo and regioselective opening of ethereal carbon-oxygen bonds by monochloroborane-dimethylsulfide
Bovicelli, Paolo,Mincione, Enrico,Ortaggi, Giancarlo
, p. 3719 - 3722 (2007/10/02)
Monochloroborane-dimethylsulfide 1 is a mild chemo and regioselective reagent useful in the opening of epoxides, THP ethers, ketals and ethers.