Vicarious silylative Mukaiyama aldol reaction: a vinylogous extension.
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 alpha,beta-unsaturated-gamma-amino-delta-silyloxy carbonyl structures, in useful yields and often with an exquisite level of diastereoselection.
Dipartimento Farmaceutico, Università di Parma, Viale G. P. Usberti 27A, I-43100 Parma, Italy.
Claudio
C
Curti
Andrea
A
Sartori
Lucia
L
Battistini
Gloria
G
Rassu
Paola
P
Burreddu
Franca
F
Zanardi
Giovanni
G
Casiraghi
D000447:Aldehydes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D014753:Vinyl Compounds; C116609:3-hydroxybutanal