Synfacts 2018; 14(11): 1143
DOI: 10.1055/s-0037-1611078
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Functionalization of Primary C–H Bonds

Rezensent(en):
Mark Lautens
,
José F. Rodríguez
Liao K, Yang Y.-F, Li Y, Sanders JN, Houk KN, Musaev DG, Davies HM. L. * Emory University, Atlanta and University of California, Los Angeles, USA; Zheijang University of Technology, Hangzhou, P. R. of China
Design of Catalysts for Site-Selective and Enantioselective Functionalization of Non-activated Primary C–H Bonds.

Nat. Chem. 2018;
10: 1048-1055
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
18.Oktober 2018 (online)

 

Significance

The authors previously described Rh-catalyzed functionalizations of secondary or tertiary C–H bonds (Liao et al. Nature 2016, 533, 230; Liao et al. Nature 2017, 551, 609). By tuning the catalyst, non-activated primary C–H bonds are functionalized with excellent site and enantio­selectivities.


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Comment

Subjecting chiral substrates to the reaction conditions allows access to either set of ­diastereomeric products when the appropriate catalyst enantiomer is employed. Stigmasteryl ­acetate could be selectively functionalized at its most sterically accessible primary C–H bond.


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