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.
Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of alpha,beta-unsaturated gamma-butyrolactam synthons / Curti, Claudio; Sartori, Andrea; Battistini, Lucia; Rassu, G.; Zanardi, Franca; Casiraghi, Giovanni. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 50:(2009), pp. 3428-3431. [10.1016/j.tetlet.2009.02.181]
Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of alpha,beta-unsaturated gamma-butyrolactam synthons
CURTI, Claudio;SARTORI, Andrea;BATTISTINI, Lucia;ZANARDI, Franca;CASIRAGHI, Giovanni
2009-01-01
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.File | Dimensione | Formato | |
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