A new Horner-Wadsworth-Emmons type coupling reaction between nonstabilized β-hydroxy phosphonates and aldehydes or ketones

JF Reichwein, BL Pagenkopf

Index: Reichwein, John F.; Pagenkopf, Brian L. Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1821 - 1824

Full Text: HTML

Citation Number: 30

Abstract

Treatment of nonstabilized β-hydroxy phosphonic acid mono methyl esters with diisopropyl carbodiimide at ambient temperature leads to clean stereospecific elimination. The phosphonic acid mono alkyl esters are accessible by the selective partial saponification of dimethyl or diethyl alkyl phosphonates with NaOH or MgBr2. Isolated yields over both hydrolysis and elimination steps average 55-75%.

~82%

~75%

Synthesis of β-hydroxyphosphonates by iron-catalyzed oxidati...

[Taniguchi, Tsuyoshi; Idota, Atsushi; Yokoyama, Shin'Ichi; Ishibashi, Hiroyuki Tetrahedron Letters, 2011 , vol. 52, # 37 p. 4768 - 4770]

Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkane...

[Zurawinski, Remigiusz; Nakamura, Kaoru; Drabowicz, Jozef; Kielbasinski, Piotr; Mikolajczyk, Marian Tetrahedron Asymmetry, 2001 , vol. 12, # 22 p. 3139 - 3145]

Reformatsky reactions with SmI 2 in catalytic amount

[Orsini, Fulvia; Lucci, Elvira Maria Tetrahedron Letters, 2005 , vol. 46, # 11 p. 1909 - 1911]