呋喃与唑烷酮取代的氧杂丙烯之间的（4 + 3）环加成的区域选择性。
Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls.
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
出版信息
Org Lett. 2010 Dec 3;12(23):5506-9. doi: 10.1021/ol1023745. Epub 2010 Nov 4.
Abstract
The (4 + 3) cycloadditions of oxazolidinone-substituted oxyallyls and unsymmetrically substituted furans lead to syn regioselectivity when the furan has a 2-Me or 2-COOR substituent, while anti regioselectivity is obtained with a 3-Me or 3-COOR group. DFT calculations are performed to explain the selectivities. The reactivities and regioselectivities are consistent with the ambiphilic reactivity of amino-oxyallyls with furans.
摘要
（4 + 3）环加成反应的恶唑烷酮取代的氧杂丙烯和不对称取代的呋喃导致顺式区域选择性，当呋喃具有 2-Me 或 2-COOR 取代基时，而反式区域选择性则得到 3-Me 或 3-COOR 基团。进行了 DFT 计算以解释选择性。反应性和区域选择性与氨基-氧杂丙烯与呋喃的两性反应性一致。
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