Theoretical study of intramolecular aldol condensation of 1, 6-diketones: Trimethylsilyl substituent effect

JP Bouillon, C Portella, J Bouquant…

Index: Bouillon, Jean-Philippe; Portella, Charles; Bouquant, James; Humbel, Stephane Journal of Organic Chemistry, 2000 , vol. 65, # 18 p. 5823 - 5830

Full Text: HTML

Citation Number: 21

Abstract

Diastereoselective intramolecular aldol condensations are investigated in an experimental and computational study of 1, 6-diketones. Ab initio results show the importance of the acid medium and disapprove the possibility of a spontaneous cyclization, even for silylated compounds. The combination of both experimental and computational approaches brings valuable information on the mechanism and on the selectivity of the aldol reaction. It is ...

Related Articles:

Iridium complex-catalyzed addition of water and alcohols to non-activated terminal alkynes

[Hirabayashi, Tomotaka; Okimoto, Yoshio; Saito, Akiyo; Morita, Masao; Sakaguchi, Satoshi; Ishii, Yasutaka Tetrahedron, 2006 , vol. 62, # 10 p. 2231 - 2234]

Efficient synthesis of 2-methyl-1-cyclopentene-1-carboxylic acid

[Harding, Kenn E.; Clement, Katherine S.; Gilbert, John C.; Wiechman, Barry Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 2049 - 2050]

(Trimethylsilyl) cyclopentene annulation: a regiocontrolled approach to the synthesis of five-membered rings

[Danheiser, Rick L.; Carini, David J.; Basak, Ajoy Journal of the American Chemical Society, 1981 , vol. 103, # 6 p. 1604 - 1606]

Hydration of alkynes in anhydrous medium with formic acid as water donor

[Menashe, Naim; Shvo, Youval Journal of Organic Chemistry, 1993 , vol. 58, # 26 p. 7434 - 7439]

Facile synthesis of 1, 3-diacetyl-2-methylcyclopentene a versatile synthetic intermediate.

[Pardo, Roselyne; Santelli, Maurice Tetrahedron Letters, 1981 , vol. 22, # 39 p. 3843 - 3846]

More Articles...