Rhodium-catalyzed asymmetric tandem cyclization for efficient and rapid access to underexplored heterocyclic tertiary allylic alcohols containing a tetrasubstituted olefin.
The first Rh-catalyzed asymmetric tandem cyclization of nitrogen- or oxygen-bridged 5-alkynones with arylboronic acids was achieved. The simple catalytic system involving a rhodium(I) complex with readily available chiral BINAP ligand promotes the reaction to proceed in a highly stereocontrolled manner. This protocol provides a very reliable and practical access to a variety of chiral heterocyclic tertiary allylic alcohols possessing a tetrasubstituted carbon stereocenter and an all-carbon tetrasubstituted olefin functionality in good yields with great enantioselectivities up to 99% ee.
State key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
Yi
Y
Li
Ming-Hua
MH
Xu
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D001897:Boronic Acids; D007659:Ketones; D008024:Ligands; D020005:Propanols; C006463:allyl alcohol; D012238:Rhodium