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DOI: 10.1055/s-0042-1753261
Synthesis of Diastereo- and Enantioenriched Homoallylic Alcohols with a Chiral CF3- and F-Bound Carbon
Diastereo- and Enantioselective Synthesis of Compounds with a Trifluoromethyl- and Fluoro-Substituted Carbon Centre.
Nat. Chem. 2022;
14: 1459-1469
DOI: 10.1038/s41557-022-01054-4.
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Significance
Hoveyda and coworkers report a regio-, diastereo- and enantioselective reaction between polyfluoro allylboronates and aldehydes. Diastereomeric polyfluoro monosaccharides were accessible from the homoallylic alcohols generated from the authors’ catalyst-controlled methodology, and a known substrate-controlled route.
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Comment
The CF3 and F substituents are important for the γ-selectivity, as α-selectivity resulting from direct allyl addition is observed when the F is replaced with an H atom. These substituents are also responsible for unusual preferential benzylation at the 2° over 1° alcohol, in one of the intermediates leading to the final pyranoside.
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Publication History
Article published online:
17 January 2023
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