Abstract
A one‐pot three‐step sequence involving Rh‐catalyzed alkene hydroacylation, sulfide elimination and Rh‐catalyzed aryl boronic acid conjugate addition gave products of traceless chelation‐controlled hydroacylation employing alkyl aldehydes. The stereodefined β‐aryl ketones were obtained in good yields with excellent control of enantioselectivity. Good variation of all three reaction components is possible.
Highlights
Kenyl- and alkyl-substituted aldehydes all proving to be excellent reaction partners.[3k–n] To extend the utility of these methods, our laboratory has shown that alkenyl- and aryl-derived Schelating aldehydes are useful substrates for a series of tandem catalytic processes that deliver traceless hydroacylation products (Scheme 1 a).[8]
Of the many ligands reported for the rhodium-catalyzed 1,4-addition of aryl boronic acids to enones,[10] catalysts generated from dienes L1 and L2 both delivered enantiomerically enriched ketone 4 a in good yields with excellent selectivities [Eq (3)].[11]
We examined the scope of the reaction with respect to the alkene substrate, employing aldehyde 1 a and para-methoxyphenylboronic acid as the two remaining components (Table 3)
Summary
Kenyl- and alkyl-substituted aldehydes all proving to be excellent reaction partners.[3k–n] To extend the utility of these methods, our laboratory has shown that alkenyl- and aryl-derived Schelating aldehydes are useful substrates for a series of tandem catalytic processes that deliver traceless hydroacylation products (Scheme 1 a).[8]. Of the many ligands reported for the rhodium-catalyzed 1,4-addition of aryl boronic acids to enones,[10] catalysts generated from dienes L1 and L2 both delivered enantiomerically enriched ketone 4 a in good yields with excellent selectivities [Eq (3)].[11]
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