Tetrahedron letters

An easy synthesis of the 2-phenylsulfonyl-substituted allylic bromides and acetates and their reactivity towards nucleophiles

P Auvray, P Knochel, JF Normant

Index: Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron Letters, 1986 , vol. 27, # 42 p. 5095 - 5098

Full Text: HTML

Citation Number: 48

Abstract

The reaction of phenyl vinyl sulfone with various aldehydes in the presence of a catalytic amount of DABCO furnishes in good yields teh corresponding 2-phenylsulfonyl-substituted alcohols which can be easily converted into their acetates or into their allylically rearranged bromides . These reagents, in turn, react with nucleophides (ketone enolates and cuprates) with an allylic rearrangement (S N 2′ mechanism) to give the functionalized unsaturated sulfones and . ...

Related Articles:

Heterodimerization of olefins. 1. Hydrovinylation reactions of olefins that are amenable to asymmetric catalysis

[RajanBabu; Nomura, Nobuyoshi; Jin, Jian; Nandi, Malay; Park, Haengsoon; Sun, Xiufeng Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8431 - 8446]

Exploring palladium nanoparticles protected with alkanethiolates functionalized with organometallic units as potential catalysts for sequential reactions

[Friederici, Mario; Angurell, Inmaculada; Rossell, Oriol; Seco, Miquel; Muller, Guillermo Journal of Molecular Catalysis A: Chemical, 2013 , vol. 376, p. 7 - 12]

Methylaluminum bis (4-bromo-2, 6-di-tert-butylphenoxide) as a key reagent for effecting primary. alpha.-alkylation of carbonyl compounds

[Maruoka, Keiji; Sato, Junko; Yamamoto, Hisashi Journal of the American Chemical Society, 1992 , vol. 114, # 11 p. 4422 - 4423]

Selective hydrovinylation of styrene in a membrane reactor: use of carbosilane dendrimers with hemilabile P, O ligands

[Hovestad, Neldes J.; Eggeling, Eva B.; Heidbuechel, H. Joerg; Jastrzebski, Johann T. B. H.; Kragl, Udo; Keim, Wilhelm; Vogt, Dieter; Van Koten, Gerard Angewandte Chemie - International Edition, 1999 , vol. 38, # 11 p. 1655 - 1658]

Copper-catalyzed reactions of organotitanium reagents. Highly selective SN 2′-allylation and conjugate addition

[Arai, Masayuki; Lipshutz, Bruce H.; Nakamura, Eiichi Tetrahedron, 1992 , vol. 48, # 27 p. 5709 - 5718]

More Articles...