Amatov T,
Tsuji N,
Maji R,
Schreyer L,
Zhou H,
Leutzsch M,
List B.
*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany and Hokkaido
University, Sapporo, Japan
Confinement-Controlled, either
syn- or
anti-Selective Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes.
J. Am. Chem. Soc. 2021;
143: 14475-14481
DOI:
10.1021/jacs.1c07447
Key words
confinement - asymmetric catalysis - stereoselectivity - Mukaiyama reaction
Significance
List and co-workers report an asymmetric Mukaiyama aldolization controlled by a confined
chiral imidodiphosphorimidate catalyst. By using catalysts 1 and 2, syn- or anti-aldol products can be obtained from (E)- or (Z)-enolsilanes, respectively, in high yields and with high diastereo- and enantioselectivities.
Comment
Compared with the reported pioneering work (S. E. Denmark, S. K. Ghosh Angew. Chem. Int. Ed.
2001, 40, 4759), this method presents an improved, fully atom- and step-economic strategy.
Ultimately, it could streamline the syntheses of complex oligopropionates.
