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Synfacts 2021; 17(11): 1257
DOI: 10.1055/s-0041-1737044
Organo- and Biocatalysis

Catalytic Asymmetric Aldolization of Propanal Enol Silanes

Authors

    Contributor(s):

  • Benjamin List

  • Yihang Li

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
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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.


 

 

Publication History

Article published online:
19 October 2021

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