期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 21, 页码 10573-10587出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo401377a
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资金
- Boston College
- ACS Petroleum Research Fund [5001009]
This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C-H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (similar to 30 USD/kg). The method forms di-, tri-, and even tetra-substituted acetones with high efficiency, and it has streamlined a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.
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