期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 5, 页码 2742-2749出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja210388g
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资金
- NIHGMS [RO1 GM073932]
- Amgen
- Novartis
- Fonds Quebecois de la Recherche sur la Nature et les Technologies (FQRNT)
The discovery of complementary methods for enantioselective transition metal-catalyzed cyclization with silyloxyenynes has been accomplished using chiral phosphine ligands. Under palladium catalysis, 1,6-silyloxyenynes bearing a terminal alkyne led to the desired five-membered ring with high enantioselectivities (up to 91% ee). As for reactions under cationic gold catalysis, 1,6- and 1,5-silyloxyenynes bearing an internal alkyne furnished the chiral cyclopentane derivatives with excellent enantiomeric excess (up to 94% ee). Modification of the substrate by incorporating an alpha,beta-unsaturation led to the discovery of a tandem cyclization. Remarkably, using silyloxy-1,3-dien-7-ynes under gold catalysis conditions provided the bicyclic derivatives with excellent diastereo- and enantioselectivities (up to >20:1 dr and 99% ee).
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