Application of the intramolecular aza-Wittig reaction to the synthesis of vinylogous urethanes and amides

PH Lambert, M Vaultier, R Carrié

Index: Lambert, P. H.; Vaultier, M.; Carrie, R. Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5352 - 5356

Full Text: HTML

Citation Number: 68

Abstract

The treatment of o-azido P-dicarbonyl derivatives with 1 equiv of triphenylphosphine leads to a transient phosphinimine (Staudinger reaction), which cyclizes into vinylogous urethanes and amides via an intramolecular am-Wittig reaction in excellent yields. The starting azides were obtained by a nucleophilic substitution by NaN3 in MezSO on the corresponding w- halo 8-dicarbonyl derivatives that were accessible by the y-alkylation of P-dicarbonyl ...

Related Articles:

Silver??Catalyzed Hydroamination: Synthesis of N??Bridgehead Pyrroles, Incorporating a Protection??Deprotection Strategy for Preparation of Cyclic Secondary …

[Robinson, Ross S.; Dovey, Martin C.; Gravestock, David European Journal of Organic Chemistry, 2005 , # 3 p. 505 - 511]

A versatile route to β-enamino esters by acylation of lithium enamines with diethyl carbonate or benzyl chloroformate

[Bartoli, Giuseppe; Cimarelli, Cristina; Dalpozzo, Renato; Palmieri, Gianni Tetrahedron, 1995 , vol. 51, # 31 p. 8613 - 8622]

Thermolyse des β-énaminodiesters cycliques: Accès à divers β-énaminoesters, β-énaminothioesters et β-enaminoamides.

[Celerier, J. P.; Maitte, P. Tetrahedron Letters, 1981 , vol. 22, p. 963 - 964]

Chemoselective intramolecular alkylation of the blaise reaction intermediates: tandem one-pot synthesis of exo-cyclic enaminoesters and their applications toward the …

[Kim, Ju Hyun; Shin, Hyunik; Lee, Sang-Gi Journal of Organic Chemistry, 2012 , vol. 77, # 3 p. 1560 - 1565]

Copper-catalyzed intramolecular N-vinylation of sulfonamides: general and efficient synthesis of heterocyclic enamines and macrolactams

[Zhao, Mei-Xin; Wang, Mei-Xiang; Yu, Chu-Yi; Huang, Zhi-Tang; Fleet, George W. J. Journal of Organic Chemistry, 2004 , vol. 69, # 3 p. 997 - 1000]

More Articles...