A new entry to β-hydroxyphosphonates:: the SMI2-mediated reaction of diethyl iodomethylphosphonate with carbonyl compounds

被引：10

作者：

Orsini, F ^{[1
]}

Caselli, A ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 40期

关键词：

beta-hydroxyphosphonates; samarium iodide;

D O I：

10.1016/S0040-4039(02)01539-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of samarium iodide alpha-halophosphonates react with aliphatic carbonyl compounds (aldehydes and ketones) to afford beta-hydroxyphosphonates in fairly good yields under neutral and mild conditions. Lower yields are obtained with aromatic carbonyl compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7255 / 7257

页数：3

共 4 条

[1] SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones:: a highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl) diphosphate
Orsini, F
Caselli, A
TETRAHEDRON LETTERS, 2002, 43 (40) : 7259 - 7261
[2] SmI2-mediated reduction of α-functionalised amides:: Highly enantiospecific access to an atropisomeric amide
Hughes, AD
Simpkins, NS
SYNLETT, 1998, (09) : 967 - +
[3] SmI2-mediated C-alkylation of Ketones with Alcohols under Microwave Conditions: A Novel Route to Alkylated Ketones
Pawar, Gaurav
Ghouse, Shaik Mahammad
Kar, Swayamsiddha
Chelli, Sai Manohar
Dannarm, Srinivas Reddy
Gour, Jitendra
Sonti, Rajesh
Nanduri, Srinivas
CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (08)
[4] Synthetic studies on polyoxypeptins:: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline using SmI2-mediated cyclization
Makino, K
Kondoh, A
Hamada, Y
TETRAHEDRON LETTERS, 2002, 43 (26) : 4695 - 4698

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