Gold-Catalyzed Sequential Alkyne Activation for the Synthesis of 4,6-Disubstituted Phosphorus 2-Pyrones

  • Mo, Juntae
  • Kang, Dongjin
  • Eom, Dahan
  • Kim, Sung Hong
  • Lee, Phil Ho
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초록

Tandem gold-catalyzed addition of alkynyl phosphonic acid monoethyl esters to terminal alkynes and cyclization were developed for the synthesis of 4,6-disubstituted phosphorus 2-pyrones in one reaction vessel based on the concept of sequential alkyne activation. Alkynyl enol phosphonates were selectively obtained through the gold-catalyzed addition reaction in the presence of a catalytic amount of triethylamine. Also, gold-catalyzed cyclization of alkynyl enol phosphonates was successful in giving a variety of 4,6-disubstituted phosphorus 2-pyrones.

키워드

ALPHA-PYRONESABSOLUTE-CONFIGURATIONADDITION-REACTIONTERMINAL ALKYNESNATURAL-PRODUCTSACIDCYCLIZATIONANALOGSD-3
제목
Gold-Catalyzed Sequential Alkyne Activation for the Synthesis of 4,6-Disubstituted Phosphorus 2-Pyrones
저자
Mo, JuntaeKang, DongjinEom, DahanKim, Sung HongLee, Phil Ho
DOI
10.1021/ol3029274
발행일
2013-01-04
유형
Article
저널명
Organic Letters
15
1
페이지
26 ~ 29