Virtually perfect transmittal of the enolate reactivity up to five conjugated double bonds from the origin allows a series of furan-based silyloxypolyenes to add to aldehyde carbonyls at the most distant point of the molecule. Denmark’s axially chiral bisphosphoramide/SiCl4 combination catalyzes these scantly precedented, long-range Mukaiyama-type vinylogous aldol reactions efficiently, providing a palette of extended γ-alkylidene butenolide carbinols with complete ω-site selectivity and good to excellent levels of enantioselectivity.
Catalytic, Asymmetric Hypervinylogous Mukaiyama Aldol Reactions of Extended Furan-Based Silyl Enolates / Curti, Claudio; Battistini, Lucia; Sartori, Andrea; Lodola, Alessio; Mor, Marco; Rassu, G.; Pelosi, Giorgio; Zanardi, Franca; Casiraghi, Giovanni. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 13:(2011), pp. 4738-4741. [10.1021/ol2020626]
Catalytic, Asymmetric Hypervinylogous Mukaiyama Aldol Reactions of Extended Furan-Based Silyl Enolates
CURTI, Claudio;BATTISTINI, Lucia;SARTORI, Andrea;LODOLA, Alessio;MOR, Marco;PELOSI, Giorgio;ZANARDI, Franca;CASIRAGHI, Giovanni
2011-01-01
Abstract
Virtually perfect transmittal of the enolate reactivity up to five conjugated double bonds from the origin allows a series of furan-based silyloxypolyenes to add to aldehyde carbonyls at the most distant point of the molecule. Denmark’s axially chiral bisphosphoramide/SiCl4 combination catalyzes these scantly precedented, long-range Mukaiyama-type vinylogous aldol reactions efficiently, providing a palette of extended γ-alkylidene butenolide carbinols with complete ω-site selectivity and good to excellent levels of enantioselectivity.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
