Three-Component Coupling of Acylphosphonates and Two Carbonyl Compounds Promoted by Low-Valent Samariums: One-Pot Synthesis of β-Hydroxyphosphonates
- 29 December 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (2) , 475-481
- https://doi.org/10.1021/jo991357s
Abstract
Three-component coupling of acylphosphonates and two carbonyl compounds leading to β-hydroxyphosphonates has been achieved with low-valent samariums. Thus, acylphosphonates reacted with aldehydes in the presence of semicatalytic amounts of samarium metal or SmI2 to give acyloxyphosphonates in good yields. The second coupling reaction of the acyloxyphosphonates with aldehydes or ketones promoted by SmI2 afforded β-hydroxyphosphonates instead of olefins. Moreover, these two reactions could be carried out in one pot.Keywords
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