Tetrahedron

Ultrasound-accelerated synthesis of chiral allylic alcohols promoted by indium metal

JS Yadav, BVS Reddy, KS Reddy

Index: Yadav; Reddy; Srinivasa Reddy Tetrahedron, 2003 , vol. 59, # 28 p. 5333 - 5336

Full Text: HTML

Citation Number: 23

Abstract

The 2-iodomethyl-O-isopropylidine acetals undergo smoothly β-elimination by indium metal in methanol under sonication to afford the corresponding allylic alcohols in excellent yields with high selectivity. This method tolerates both acid and base labile functional and protecting groups and also free hydroxyl groups present in the molecule. Improved yields and enhanced rates are the remarkable features obtained by ultrasound.

Related Articles:

Single electron transfer mechanism in the reaction of 1, 3-dithianyllithium and alkyl iodides

[Juaristi, Eusebio; Jimenez-Vazquez, Hugo A. Journal of Organic Chemistry, 1991 , vol. 56, # 4 p. 1623 - 1630]

Titanium tetrachloride promoted reactions of allylic trimethylsilanes and oxetane

[Carr, Steve A.; Weber, William P. Journal of Organic Chemistry, 1985 , vol. 50, # 15 p. 2782 - 2785]

Selective dehydration of alkanediols into unsaturated alcohols over rare earth oxide catalysts

[Yamanaka, Tohr; Imai, Takashi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 5 p. 1585 - 1586]

Facile Synthesis of Spirocyclic Systems through the Intramolecular Addition of Ketyl Radicals via the Sodium/Ammonia Reduction of δ, ε-Unsaturated Carboxylic …

[Journal of Organic Chemistry, , vol. 63, # 9 p. 3141 - 3146]

Alkyl Radical Generation in Water under Ambient Conditions—A New Look at the Guareschi Reaction of 1897

[Angewandte Chemie - International Edition, , vol. 46, # 40 p. 7655 - 7658]

More Articles...