期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 17, 页码 6772-6779出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo801098z
关键词
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资金
- NIH [GM069559]
- Director and Office of Energy Research, Office of Basic Energy Sciences, Chemical Sciences Division, U.S. Department of Energy [DE-AC03-76SF00098]
- Eisai Co., Ltd.
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)(2)](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 7 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.
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