@article{29d66b869eb444369ce85f05f54614b8,
title = "Synthetic utility of epoxides for chiral functionalization of isoxazoles",
abstract = "The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100% inversion at the benzylic carbon to afford the (S)-alcohol (4b).",
author = "Nelson, {Jared K.} and Burns, {Christopher T.} and Smith, {Miles P.} and Brendan Twamley and Natale, {N. R.}",
note = "Funding Information: The authors thank the National Institute of Neurological Disease and Stroke for the continuing support of Grant NS38444, and P20 RR015583. J.K.N. acknowledges INBRE Grant P20 RR16454 and the Malcolm and Carol Renfrew Scholarship Endowment, University of Idaho. The Bruker (Siemens) smart apex diffraction facility was established at the University of Idaho with the assistance of the nsf-epscor program and the M. J. Murdock Charitable Trust, Vancouver, WA, USA. ",
year = "2008",
month = may,
day = "5",
doi = "10.1016/j.tetlet.2008.03.059",
language = "English",
volume = "49",
pages = "3078--3082",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Ltd",
number = "19",
}