77287-62-8Relevant academic research and scientific papers
Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides
Daniel, Paige E.,Weber, Alexandria E.,Malcolmson, Steven J.
supporting information, p. 3490 - 3493 (2017/07/15)
We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.
Metalation of o-Halostyrene Oxides. Preparation of Benzocyclobutenols
Akguen, Eyup,Glinski, Margaret B.,Dhawan, Kasturi L.,Durst, Tony
, p. 2730 - 2734 (2007/10/02)
o-Bromo- and o-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBr2 in THF or ether at -78 deg C, followed by warming to room temperature.The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization.Benzocyclobutenol formation was not successful in the case of o-halostilbene oxides.
