@article{6cd0adabb334498ea021bdcf0965a04c,
title = "4+3 Cycloaddition reactions of halogen-substituted cyclohexenyl oxyallylic cations",
abstract = "2,6-Dibromo- and 2,2-dichlorocyclohexanone react with base in the presence of various dienes to give 4+3 cycloadducts in fair to good yields. Preliminary studies of the cycloadducts suggest that they are unstable and are recalcitrant to nucleophilic addition and cross-metathesis. However, the LAH reduction products undergo a quasi-Favorskii rearrangement upon treatment with potassium hydride and one cycloadduct derivative was dehalogenated using radical chemistry.",
author = "Michael Harmata and Lixin Shao and Laszlo K{\"u}rti and Asitha Abeywardane",
note = "Funding Information: The chemistryd escribedh ereino ffersrapid accessto complexp olycyclics tructureisn a stereoselectivaen d regioselectivfea shion.The combinatioonf a 4+3 cycloaddition/quasi-Favorsrekaiic tionm akesh alogen-substituteodx yallylicc ationss ynthetice quivalentosf cyclopentencea rboxaldehydeAs.t least in some casest, his allows accesst o Diels-Alderc ycloadductws hichcould not be preparedd irectlyusing a more direct 4+2 cycloadditionap proach.F urtherd evelopmenotf this methodologayn de xplorationo f the bridgeheahda lide reactivityo f theses ystemsis in progressa ndr esultsw ill be reportedin due course1. 3,14 AcknowledgementsT: his work was supportedb y the National Science Foundation. MH thanks the Alexandery on HumboldtF oundationfo r a fellowshipa ndP rofessorsR einhardB rtickner( thenG rttingenn, ow Freiburg)a ndLutz F. Tietze (Grttingenf)o r their hospitality.W e thank the National ScienceF oundationfo r partial supporto f the NMR (PCM-8115599f)a cilityat the Universityo f Missouri-Columbiaan dfor partial funding for the purchaseo f a 500 MHz spectromete(Cr HE-89-08304a) ndan X-ray diffractomete(rC HE-90-11804).",
year = "1999",
month = feb,
day = "5",
doi = "10.1016/S0040-4039(98)02629-X",
language = "English (US)",
volume = "40",
pages = "1075--1078",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "6",
}