Department of Chemistry, Davenport Chemical Laboratories, 80 St. George Street, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
Org Lett. 2012 Sep 21;14(18):4806-9. doi: 10.1021/ol302111y. Epub 2012 Sep 6.
A diastereoselective approach to isochromans and chromans via Pd(0)-catalyzed carboiodination is reported. The transformations using this methodology display excellent yields and diastereoselectivities as well as broad functional group compatibility. The selectivity observed in these cyclizations, forming isochroman or chroman targets, is postulated to originate from the minimization of A(1,2) strain and axial-axial interactions, respectively. This method has also been used to highlight the concept of reversible oxidative addition to carbon-iodine bonds in polyiodinated substrates.
本文报道了钯（0）催化的碳碘键插入反应实现异苯并呋喃和色满的对映选择性构建。该方法具有优秀的收率和对映选择性，以及广泛的官能团兼容性。这些环化反应中观察到的选择性，形成异苯并呋喃或色满目标物，据推测分别源于 A(1,2)应变和轴向-轴向相互作用的最小化。该方法还用于强调多碘代底物中碳-碘键可逆氧化加成的概念。
