Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of α,β-unsaturated γ-butyrolactam synthons
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- 作者：Claudio Curti ; Andrea Sartori ; Lucia Battistini ; Gloria Rassu ; Franca Zanardi ; Giovanni Casiraghi
- 关键词：Vinylogous aldol reaction ; Lewis base catalysis ; Pyrrole-based dienoxy silanes ; Enantioselective synthesis
- 刊名：Tetrahedron Letters
- 出版年：2009
- 出版时间：1 July 2009
- 年：2009
- 卷：50
- 期：26
- 页码：3428-3431
- 全文大小：1142 K
文摘
A practical, catalytic and enantioselective vinylogous Mukaiyama aldol reaction between 2-silyloxypyrrole donors and aromatic or heteroaromatic aldehyde acceptors is described. Using an enantiopure bisphosphoramide catalyst in conjunction with SiCl4, a variety of α,β-unsaturated-δ-hydroxylated γ-butyrolactam compounds were synthesized in high yields and with good to excellent levels of site-, diastereo- and enantioselectivity.