New approaches towards the synthesis of alkenes using the Horner-Wadsworth-Emmons (HWE) reaction as the key step

K Bodman, S Has-Becker, O Reiser

Index: Bodman, Kerstin; Has-Becker, Shenay; Reiser, Oliver Phosphorus, Sulfur and Silicon and Related Elements, 1999 , vol. 144-146, p. 173 - 176

Full Text: HTML

Citation Number: 2

Abstract

Leading from our work in asymmetric alkene synthesis it was discovered that the alkenylatio of aldehydes with phosphonates proceeds smoothly at room temperature in the absence of Lewis acid using triethylamine as the base if the reaction is carried out at a pressure of 8 kbar. Based on this protoco a new domino process was developed, combining the HWE reaction with a Heck coupling, thus allowing the one pot synthesis of trisubstituted alkenes.

Related Articles:

Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone

[Oku, Akira; Abe, Manabu; Iwamoto, Masaharu Journal of Organic Chemistry, 1994 , vol. 59, # 24 p. 7445 - 7452]

Stereoselective preparation of highly functionalized (Z)-3-copper enoates by an iodine-copper exchange reaction

[Yang, Xiaoyin; Knochel, Paul Synthesis, 2006 , # 13 p. 2167 - 2172]

Conjugate reduction of. alpha.,. beta.-acetylenic ketones and esters by diisobutylaluminum hydride-hexamethylphosphoric triamide

[Journal of Organic Chemistry, , vol. 52, # 8 p. 1624 - 1627]

A convenient one-pot PCC oxidation-wittig reaction of alcohols

[Bressette, Andrew R.; Glover IV, Louis C. Synlett, 2004 , # 4 p. 738 - 740]

The first example of a catalytic Wittig-type reaction. Tri-n-butylarsine-catalyzed olefination in the presence of triphenyl phosphite

[Shi, Lilan; Wang, Weibo; Wang, Yucheng; Huang, Yao-Zeng Journal of Organic Chemistry, 1989 , vol. 54, # 9 p. 2027 - 2028]

More Articles...