Lewis 碱辅助的 Brønsted 碱催化：烯丙基砜的直接区域选择性不对称乙烯基烷基化反应。
Lewis base assisted Brønsted base catalysis: direct regioselective asymmetric vinylogous alkylation of allylic sulfones.
机构信息
Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, PR China.
出版信息
Chemistry. 2011 Aug 16;17(34):9489-93. doi: 10.1002/chem.201100534. Epub 2011 Jun 30.
A Lewis base assisted Brønsted base catalysis (LBABB) strategy is applied for direct asymmetric vinylogous alkylation of allylic sulfones with Morita-Baylis-Hillman (MBH) carbonates, in which a strong Brønsted base, tert-butoxy anion, generated in situ from a tertiary amine catalyst and MBH carbonate, is crucial in activating unstabilized nucleophiles. The γ-regioselective alkylation products were obtained with good to excellent enantiomeric excess values when catalyzed by a modified cinchona alkaloid.
路易斯碱辅助的布朗斯特碱催化（LBABB）策略被应用于烯丙基砜与 Morita-Baylis-Hillman（MBH）碳酸酯的直接不对称乙烯基烷基化反应中，其中原位生成的强布朗斯特碱叔丁氧基阴离子由三级胺催化剂和 MBH 碳酸酯产生，这对于活化未稳定的亲核试剂至关重要。当用改良的金鸡纳生物碱催化时，γ-区域选择性烷基化产物具有良好到优异的对映体过量值。
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