期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 14, 页码 5380-5382出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo070472x
关键词
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资金
- NIGMS NIH HHS [GM064559] Funding Source: Medline
A catalytic, asymmetric process for the synthesis of 1,4-benzoxazinones from o-benzoquinone imides and ketene enolates is reported. Addition of Lewis acids (Zn(OTf)(2), In(OTf)(3), and in particular Sc(OTf)(3)) creates a bifunctional catalytic system that dramatically increases the reaction rate and the yield of these non-natural amino acid precursors while preserving the remarkable enantioselectivity inherent to the reaction. Cocatalyst Sc(OTf)(3) increases the yield by up to 42% while producing products in > 99% ee.
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