Three-component coupling of acylphosphonates and two carbonyl compounds promoted by low-valent samariums: One-pot synthesis of β-hydroxyphosphonates

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 475-481

  Takaki, Ken ^a   Itono, Yuichiro ^a   Nagafuji, Akihiro ^a   Naito, Yoji ^a   Shishido, Tetsuya ^a   Takehira, Katsuomi ^a   Makioka, Yoshikazu ^b   Taniguchi, Yuki ^b   Fujiwara, Yuzo ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SAMARIUM;

ARTICLE; CATALYSIS; JAPAN; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0034723301     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991357s     Document Type: Article

References (24)

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19. for example, the reaction of 1a with benzophenone in the presence of Sm metal (1 equiv) gave diphenylmethyl tolyl ketone and diphenylhydroxymethyl tolyl ketone in 73% and 20% yields, respectively. 2-Adamantyl phenyl ketone was prepared in 30% yield from 1b and 2-adamantanone; However, the reaction with ketones having α-hydrogens such as cyclohexanone gave a complex mixture.
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21. 2, 18 was formed in 51% yield, and 7 was recovered in 21% yield.
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