TY - JOUR
T1 - Alkene dioxygenation with malonoyl peroxides
T2 - synthesis of ɣ-lactones, isobenzofuranones and tetrahydrofurans
AU - Alamillo-Ferrer, Carla
AU - Karabourniotis-Sotti, Marianna
AU - Kennedy, Alan R.
AU - Campbell, Matthew
AU - Tomkinson, Nicholas C. O.
PY - 2016/6/17
Y1 - 2016/6/17
N2 - Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82% yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.
AB - Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82% yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.
KW - saturated oxygen heterocycles
KW - homoallylic alcohols
KW - carboxylic acids
UR - http://pubs.acs.org/loi/orlef7
U2 - 10.1021/acs.orglett.6b01253
DO - 10.1021/acs.orglett.6b01253
M3 - Article
SN - 1523-7060
JO - Organic Letters
JF - Organic Letters
ER -