期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 15, 页码 5345-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja910666n
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资金
- NIGMS [GM73072]
- Sloan Foundation
- Amgen
- AstraZeneca
- GlaxoSmithKline
- FQRNT (Fonds Quebecois de la Recherche sur la Nature et les Technologies)
A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivity and enantioselectivity. The presence of Ti(O/Pr)(4) as the Lewis acid allows for efficient substrate preorganization, which translates into high levels of diastereoselectivity. Additionally, we demonstrate the possibility of controlling the absolute stereochemistry of NHC-catalyzed reactions by employing a catalytic amount of a chiral Lewis acid as the unique source of optically active promoter.
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