Three-Component Coupling of Acylphosphonates and Two Carbonyl Compounds Promoted by Low-Valent Samariums: One-Pot Synthesis of β-Hydroxyphosphonates

Autor:	Yoshikazu Makioka, Ken Takaki, Akihiro Nagafuji, Yuzo Fujiwara, Tetsuya Shishido, Yuichiro Itono, Yoji Naito, Katsuomi Takehira, Yuki Taniguchi
Rok vydání:	1999
Předmět:	Samarium Coupling (electronics) Metal chemistry visual_art Organic Chemistry One-pot synthesis visual_art.visual_art_medium Organic chemistry chemistry.chemical_element Medicinal chemistry Coupling reaction
Zdroj:	The Journal of Organic Chemistry. 65:475-481
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo991357s
Popis:	Three-component coupling of acylphosphonates and two carbonyl compounds leading to beta-hydroxyphosphonates has been achieved with low-valent samariums. Thus, acylphosphonates reacted with aldehydes in the presence of semicatalytic amounts of samarium metal or SmI(2) to give acyloxyphosphonates in good yields. The second coupling reaction of the acyloxyphosphonates with aldehydes or ketones promoted by SmI(2) afforded beta-hydroxyphosphonates instead of olefins. Moreover, these two reactions could be carried out in one pot.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ce8f66cd203b7e011e94348633541b13 https://doi.org/10.1021/jo991357s Zobrazit plný text záznamu