Synthesis of optically active bifunctional building blocks through enantioselective copper-catalyzed allylic alkylation using Grignard reagents.
Enantioselective copper-catalyzed allylic alkylations were performed on allylic bromides with a protected hydroxyl or amine functional group using several Grignard reagents and Taniaphos L1 as a ligand. The terminal olefin moiety in the products was transformed into various functional groups without racemization, providing facile access to a variety of versatile bifunctional chiral building blocks.
van Zijl
Anthoni W
AW
Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747AG, Groningen, The Netherlands.
López
Fernando
F
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
D000478:Alkylation; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D000596:Amino Acids; D001965:Bromides; D003300:Copper