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Synfacts 2018; 14(11): 1143
DOI: 10.1055/s-0037-1611078
DOI: 10.1055/s-0037-1611078
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Enantioselective Functionalization of Primary C–H Bonds
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
Design of Catalysts for Site-Selective and Enantioselective Functionalization of Non-activated Primary C–H Bonds.
Nat. Chem. 2018;
10: 1048-1055
Further Information
Publication History
Publication Date:
18 October 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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