期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 11, 期 42, 页码 7301-7317出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41632a
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资金
- UCL
In this report, a thorough evaluation of the use of aerobically initiated, metal-free hydroacylation of various C=C and N=N acceptor molecules with a wide range of aldehydes is presented. The aerobic-activation conditions that have been developed are in sharp contrast to previous conditions for hydroacylation, which tend to use transition metals, peroxides that require thermal or photochemical degradation, or N-heterocyclic carbenes. The mildness of the conditions enables a number of reactions involving sensitive reaction partners and, perhaps most significantly, allows for alpha-functionalised chiral aldehydes to undergo radical-based hydroacylation with complete retention of optical purity. We also demonstrate how the resulting hydroacylation products can be transformed into other useful intermediates, such as gamma-keto-sulfonamides, sultams, sultones, cyclic N-sulfonyl imines and amides.
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