Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of α,β-unsaturated γ-butyrolactam synthons |
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Authors: | Claudio Curti Andrea Sartori Gloria Rassu Giovanni Casiraghi |
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Affiliation: | a Dipartimento Farmaceutico, Università degli Studi di Parma, Viale G. P. Usberti 27A, Parma I-43100, Italy b Istituto di Chimica Biomolecolare del CNR, Traversa La Crucca 3, Li Punti, Sassari I-07040, Italy |
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Abstract: | 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. |
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Keywords: | Vinylogous aldol reaction Lewis base catalysis Pyrrole-based dienoxy silanes Enantioselective synthesis |
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