A vinylogous, silylative, and direct variant of the venerable Mukaiyama aldol reaction has been developed. Exploiting N-Boc-pyrrol-2(5H)-one as the conjugate donor, several aldehyde and ketone acceptors were scrutinized under the guidance of suitable dual Lewis acid−Lewis base activators to provide a varied repertoire of functionality-rich α,β-unsaturated-γ-amino-δ-silyloxy carbonyl structures, in useful yields and often with an exquisite level of diastereoselection.
Vicarious Silylative Mukaiyama Aldol Reaction: A Vinylogous Extension / Curti, Claudio; Sartori, Andrea; Battistini, Lucia; Rassu, G.; Burreddu, P.; Zanardi, Franca; Casiraghi, Giovanni. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 73:(2008), pp. 5446-5451. [10.1021/jo800741c]
Vicarious Silylative Mukaiyama Aldol Reaction: A Vinylogous Extension
CURTI, Claudio;SARTORI, Andrea;BATTISTINI, Lucia;ZANARDI, Franca;CASIRAGHI, Giovanni
2008-01-01
Abstract
A vinylogous, silylative, and direct variant of the venerable Mukaiyama aldol reaction has been developed. Exploiting N-Boc-pyrrol-2(5H)-one as the conjugate donor, several aldehyde and ketone acceptors were scrutinized under the guidance of suitable dual Lewis acid−Lewis base activators to provide a varied repertoire of functionality-rich α,β-unsaturated-γ-amino-δ-silyloxy carbonyl structures, in useful yields and often with an exquisite level of diastereoselection.File | Dimensione | Formato | |
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