A stereoselective michael addition of α-lithiated phosphonates to α,β-unsaturated esters
✍ Scribed by Masahiko Yamaguchi; Yukiharu Tsukamoto; Akio Hayashi; Toru Minami
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 123 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
a-Lithiated phosphonates added to a&unsaturated t-butyl esters in 1,Gmanner giving anti-3,4-disubstituted-4-phosphorylbutanoates in high yields.
/~~%~ylam%omethyl)phosphonates were prepared from dialkyl phosphite, dibenzylamine, and formaldehyde: See; R. Tyka, Tetrahedron Lett., 1970, 677.
📜 SIMILAR VOLUMES
## Abstract For Abstract see ChemInform Abstract in Full Text.
Under a proper reaction condition, simple ester enolates add to d,e-unsaturated esters highly stereoselectively to give erythro or threoglutarates. Previously, we have shown that lithium enolates derived from simple monoesters react with fi,p-unsaturated esters to give glutarates in high yiela. 1)
We recently reported the first examples of conjugate additions of alkyl sulphoxides to unsaturated esters,\* These reactions proceed with good selectivity and provide a promising new method for carrying out
Synthetic precursors of amino phosphonic acids are aziridinyl phosphonates. These compounds can be prepared through a reaction of phosphonates 2a-e with NsONHCO 2 Et and inorganic bases involving addition of an (ethoxycarbonyl)amino group onto the double bond, via a new and easy procedure.
We have found that in the presence of fluoride ion, nitrotoluenes of type 1 undergo Michael addition to activated a, p-unsaturated esters of type 2 in good to excellent yield (Scheme 1). The generality and limitation of this reaction and its application to the chiral synthesis of benzazepine 4 are d