Copper-Catalyzed Enantioselective Domino Arylation/Semipinacol Rearrangement of Allylic Alcohols with Diaryliodonium Salts

A copper-catalyzed enantioselective arylative semipinacol rearrangement of allylic alcohols was developed. In the presence of a catalytic amount of an in situ generated chiral copper-bisoxazoline complex, reaction of allylic alcohols with diaryliodonium salts afforded spirocycloalkanones in high yields with high diastereo- and enantioselectivities. A two-point binding model engaging the carbon–carbon double bond and the proximal hydroxyl group was proposed to be responsible for the highly efficient chirality transfer.


Published in:
Chemistry - A European Journal, 23, 53, 13037-13041
Year:
2017
Publisher:
Wiley-Blackwell
ISSN:
0947-6539
Keywords:
Laboratories:




 Record created 2017-10-28, last modified 2018-09-13


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