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Synlett 2009(6): 994-998
DOI: 10.1055/s-0028-1088198
DOI: 10.1055/s-0028-1088198
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium-Catalyzed Asymmetric 1,4-Addition of Heteroaryl Cyclic Triolborate to α,β-Unsaturated Carbonyl Compounds
Further Information
Received
16 December 2008
Publication Date:
16 March 2009 (online)
Publication History
Publication Date:
16 March 2009 (online)
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Abstract
Rhodium-catalyzed asymmetric 1,4-additions of electron-deficient heteroaryl groups to α,β-unsaturated carbonyl compounds were established. The reaction resulted in very low yields due to competitive C-B bond cleavage when arylboronic acids, their pinacol esters, or potassium trifluoroborates were used. However, the corresponding lithium heteroaryl(triol)borates afforded 1,4-adducts with high enantioselectivities up to 97% in the presence of a rhodium(I) catalyst chelated with a chiral BINAP or BIPAM ligand.
Key words
heteroaryl cyclic triolborate - rhodium catalyst - asymmetric reaction - conjugate addition
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