Enantioselective Intramolecular Hydroarylation of Alkenes via Directed C-H Bond Activation
Journal Article
·
· Journal of Organic Chemistry
Highly enantioselective catalytic intramolecular ortho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using [RhCl(coe){sub 2}]{sub 2} and chiral phosphoramidite ligands. Cyclization of substrates containing 1,1- and 1,2-disubstituted as well as trisubstituted alkenes were achieved with enantioselectivities >90% ee for each substrate class. Cyclization of substrates with Z-alkene isomers proceeded much more efficiently than substrates with E-alkene isomers. This further enabled the highly stereoselective intramolecular alkylation of certain substrates containing Z/E-alkene mixtures via a Rh-catalyzed alkene isomerization with preferential cyclization of the Z-isomer.
- Research Organization:
- Ernest Orlando Lawrence Berkeley National Laboratory, Berkeley, CA (US)
- Sponsoring Organization:
- Chemical Sciences Division
- DOE Contract Number:
- AC02-05CH11231
- OSTI ID:
- 948473
- Report Number(s):
- LBNL-1511E
- Journal Information:
- Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry; ISSN 0022-3263; ISSN JOCEAH
- Country of Publication:
- United States
- Language:
- English
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