期刊
ORGANIC LETTERS
卷 10, 期 21, 页码 5091-5094出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol802147h
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资金
- National Institutes of Health [SC2 GM081064-01]
- ACS Petroleum Research Fund [PRF 45277-B1]
- Henry Dreyfus Teacher-Scholar Award
alpha-Alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R-2 = allyl) furnishes instead gamma,delta-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at -78 degrees C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R-2 = benzyl) rearranges to indanone 7 upon heating to 60 degrees C.
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