Synthesis of new C2-symmetric bioxazoles and application as chiral ligands in asymmetric hydrosilylation

Lee, Sang Gi; Lim, Chun Kyu; Song, Choong Eui; Kim, In O; Jun, Chul Ho

doi:10.1016/s0957-4166(97)00353-4

Cited by 36 publications

(9 citation statements)

References 34 publications

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“…Oxazolines 232 and 233 were prepared from (-)-norephedrine and (+)-endo-2-hydroxy-endo-3aminobornane (231) and 2fluorobenzoic acid (230) for Tsuji-Trost reactions under the conditions depicted in Scheme 40 [97,98]. Treatment of 232 and 233 with potassium diphenylphosphide gave 234 and 235, respectively.…”

Section: Synthesis Of Phosphorus-containing Oxa-zoline Ligandsmentioning

confidence: 99%

The Meyers Reaction (1994-2010)

Mortier

2011

COC

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The Meyers reaction, i.e. the nucleophilic aromatic substitution reaction between aryloxazolines with organolithium and organomagnesium reagents is a very efficient and reliable method for the formation of new carbon-carbon and carbon-heteroatom bonds. The aim of this review is to present a general overview of this reaction in chiral and racemic form, emphasizing its scope and limitations. The literature is covered since 1994.

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Section: Synthesis Of Phosphorus-containing Oxa-zoline Ligandsmentioning

confidence: 99%

The Meyers Reaction (1994-2010)

Mortier

2011

COC

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“…Indeed, drugs based on 1,2,3,4-diaminobutanediols and derivatives showed anticancer properties, and complexes of threo-2,3-diaminobutane-1,4-diol derived from mannitol were used as antitumor agents. 7 These compounds are also the precursors of bioxazoles 3 8 and bioxazolidinones 4, 9 useful for asymmetric hydrosilylation and allylic substitution. 10 Our continuing interest in utilizing tartaric acid as a chiral source for the synthesis of optically active products 11 led us to investigate an efficient construction of polyfunctionalized, N-substituted compounds 5 and of the corresponding N,O-formacetals 6 ( Figure 2).…”

Section: Figure 1 Chiral Vic-diamines 1-4mentioning

confidence: 99%

Synthesis of New Chiral Mixedcis-Tetraheterodecalines by Highly Selective Cyclization ofN,N′-Bisalkyl 2,3-Diaminobutanediols

Gras¹,

Taulier²

2006

Synthesis

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Chiral secondary vic-diamines of diaminobutanediols have been efficiently prepared from L-tartaric acid. Their selective cyclization led to cis-tetraheterodecalines having a (1S,6S)-2, 7-diaza-4,9-dioxa[4.4.0]decane core system. Enantiomerically pure vicinal diamines occur commonly in nature, with many of them having biological properties. Some of them and several synthetic vic-diamines are used as medicinal agents. 1 In the laboratory vic-diamines have found widespread use as chiral ligands in asymmetric reactions, especially C 2 -symmetric vic-diamines with their symmetry element added. 2 Moreover, with the degree of conformational freedom of chiral complexes with a transition metal being reduced in cyclic derivatives, only a few such chiral vic-diamines have been designed. For example bipyrrolidines 1 were used in the asymmetric dihydroxylation of alkenes 3 and the ligand activity of bioxazoles 2, where the two oxazoline rings are directly bonded, has been reported in Cu, Rh, Ir catalyzed asymmetric hydrosilylation of ketones, 4 cyclopropanation of olefins, 5 and transfer hydrogenation of ketones ( Figure 1). 6 Figure 1 Chiral vic-diamines 1-4Several reports show the biological importance of diaminobutanediols. Indeed, drugs based on 1,2,3,4-diaminobutanediols and derivatives showed anticancer properties, and complexes of threo-2,3-diaminobutane-1,4-diol derived from mannitol were used as antitumor agents. 7 These compounds are also the precursors of bioxazoles 3 8 and bioxazolidinones 4, 9 useful for asymmetric hydrosilylation and allylic substitution. 10

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“…Reaction mixture was stirred for 24 h at ambient temperature, solvent evaporated, and yellow oil crystallized on addition of MeOH (8.0 ml). On standing overnight in refrigerator 1 …”

Section: Dicarbomethoxy-4-phenyl-13-butadiene (13)mentioning

confidence: 99%

Comparative Study of 1,5‐Dinitrogen Schiff Bases as Potential Ligands in Palladium‐Catalyzed Allylic Alkylation.

et al. 2004

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1-(2'-Pyrido and 2'-quinolino)-(1R)-arylethylamino)-ethylidenes (7-12) were prepared as potential ligands in Pd II catalytic complexes for enantioselective allylic alkylation of 1,3-diphenyl-1-acetoxy-propene-2 (15). Alkylation with palladium complexes of 7-12 yielded 1,3-diphenyl-1-dimethylmalonyl-propene-2 (14) with enantioselectivity up to 55 % e.e. Enantioselectivity is discussed in view of the results recently reported for structurally related 1,5-bidentate dinitrogen ligands of C 1 symmetry. Reversal of enantioselectivity observed for the ligands 10 and 11 is attributed to the inversion of steric requirements in the second coordination sphere of their catalytic complexes.

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Synthesis of new C2-symmetric bioxazoles and application as chiral ligands in asymmetric hydrosilylation

Cited by 36 publications

References 34 publications

The Meyers Reaction (1994-2010)

The Meyers Reaction (1994-2010)

Synthesis of New Chiral Mixedcis-Tetraheterodecalines by Highly Selective Cyclization ofN,N′-Bisalkyl 2,3-Diaminobutanediols

Comparative Study of 1,5‐Dinitrogen Schiff Bases as Potential Ligands in Palladium‐Catalyzed Allylic Alkylation.

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