Journal
ACS CATALYSIS
Volume 13, Issue 8, Pages 5578-5583Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.3c00536
Keywords
copper; allylboration; asymmetric catalysis; allenes; multifunctional compounds; noncovalent interactions
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A catalytic asymmetric reaction involving allyl copper species with allylic gem-dichloride is reported, providing high selectivity chiral internal 1,5-dienes with (Z)-configured alkenyl boronate and alkenyl chloride. The synthetic utility of the products is demonstrated by synthesizing optically active compounds. DFT calculations reveal noncovalent substrate-ligand interactions accounting for the selectivity outcome.
A catalytic asymmetric reaction between allenes, bis(pinacolato)diboron, and allylic gem-dichlorides is reported. The method involves the coupling of a catalytically generated allyl copper species with the allylic gem-dichloride and provides chiral internal 1,5-dienes featuring (Z)-configured alkenyl boronate and alkenyl chloride units with high levels of chemo-, regio-, enantio-, and diastereoselectivity. The synthetic utility of the products is demonstrated with the synthesis of a range of optically active compounds. DFT calculations reveal key noncovalent substrate-ligand interactions that account for the enantioselectivity outcome and the diastereoselective formation of the (Z)-alkenyl chloride.
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