A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2′-alkenyl)- or benzyl-sulfonyl]-benzothiazoles.

Baudin, Jean‐Bernard; Hareau, Georges; Julia, S. A.; Ruel, O.

doi:10.1016/s0040-4039(00)92037-9

Cited by 387 publications

(176 citation statements)

References 22 publications

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“…It is notable that the catalytic system tolerates a wide variety of functional group. For example, methylthio benzothiazole (13f) that is a useful nucle-ophile for the Julia olefination 69) was converted to the sulfone 15f in 78% yield (entry 11). In this reaction, benzothiazole ring was unaffected through the reaction.…”

Section: Oxidation Of Sulfidesmentioning

confidence: 99%

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Yamada

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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IntroductionDevelopment of immobilized and insoluble metal catalysts is of great interest in recent organic chemistry. [1][2][3][4][5][6][7][8][9] The simple recovery of catalysts by filtration and their reuses resulted in enhancing the economical evaluation of the reaction. At the same time, there is a prospect that the environmental pollution caused by residual metals in the waste fluid will be decreased. Although a great deal of effort has been made to carry out such ideal reactions using immobilized metal catalysts, what seems to be lacking is the efficiency of the catalytic systems. It is obvious that the heterogeneous catalytic systems exhibit generally lower activity than the homogeneous ones. Besides, it is expected that the activity of the catalysts decreases gradually in the recycled systems because the metal species leaches away from their supports. Taking these into consideration, we decided to concentrate on developing insoluble metal catalysts which are highly active and stable. We designed that they were still effective in the use of ppm mol eq, and in the recycled use of many times in any reaction media. To achieve the challenging theme, we have focused on the amphiphilic insoluble catalysts based on a novel concept (Chart 1).Over the past few decades, a considerable numbers of study have been made on solid-phase catalysts which were immobilized with cross-linked polystyrene resins, silica gels or metals. These catalytic systems, however, generally resulted in lower catalytic activity compared with their soluble counterparts, and were often obliged to use hazardous chlorohydrocarbon solvents. [10][11][12][13][14][15] Besides, reuse of these catalysts was often difficult owing to the gradual decline of the catalytic activity. These problems made them less practical.In traditional triphase catalysts, as I have mentioned before, a catalytic species was anchored to a linker that was immobilized to a polymer resin or silica gel (Chart 1, above). In July 2005Chem. Pharm. Bull. 53(7) 723-739 (2005)

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Section: Oxidation Of Sulfidesmentioning

confidence: 99%

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Yamada

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Despite extensive experimentation, we found that numerous combinations of Pd-catalyst and ligand gave unsatisfactory yields of the biaryl product 23 (Scheme 3). The best isolated yield of coupled product 23 was Ϸ20%, which was routinely accompanied by side products resulting from alkyl group transfer from the stannane (24) and reductive removal of the iodine atom (25). Because of the fact that the Stille coupling gave undesired side products and insufficient yields, we decided that the Suzuki (35) coupling protocol was the next logical choice for constructing the biaryl bond.…”

Section: Resultsmentioning

confidence: 99%

A concise, total synthesis of the TMC-95A/B proteasome inhibitors

Albrecht

Williams

2004

Proc. Natl. Acad. Sci. U.S.A.

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A concise, total synthesis of the proteasome inhibitors TMC-95A͞B has been accomplished. The synthesis features the use of an L-serine-derived E-selective modified Julia olefination reaction to ultimately control the stereochemical outcome of the highly oxidized tryptophan fragment. Additionally, the limited use of protecting groups at a late stage of the total synthesis allowed for its completion in an efficient manner.Julia olefination ͉ Suzuki biaryl coupling ͉ Stille coupling

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“…On the other hand, the sulfone unit was prepared by Sharpless AD of the known olefinic alcohol 48, 55) and sulfone 49 was also obtained in an enantiomerically pure form via recrystallization of an intermediate. One-pot Julia coupling 51,56,57) of sulfone 49 and aldehyde 47 using KHMDS afforded olefin 50 in good yield, but E/Z selectivity was not very high (E/Z = 2:1). Because the low selectivity appeared to be caused by some chelation effects of oxygen functional groups in sulfone 49 and aldehyde 47 with potassium cation, we tried other conditions employing additives to prevent this chelation.…”

Section: Other Syntheses Of Microcarpalide Employing Rcmmentioning

confidence: 99%

“…Our synthesis of microcarpalide Our synthesis of microcarpalide is shown in Scheme 2 [6]. 49,50) Most synthetic approaches have been based on RCM, whereas we selected lactonization as a ring-closing step and Julia coupling 51) for the construction of trans-olefin. We also decided to introduce all four stereocenters using Sharpless AD.…”

Section: Other Syntheses Of Microcarpalide Employing Rcmmentioning

confidence: 99%

Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

Ishigami

2009

Bioscience, Biotechnology, and Biochemistry

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A number of 10-membered lactones have been isolated as secondary metabolites, and many of them have interesting and potent activities. Because of synthetic and biological interests, many synthetic studies of these compounds have been made. This review summarizes synthetic approaches to three natural 10-membered lactones, mueggelone, microcarpalide, and Sch 642305. Mueggelone is an inhibitor of fish development, microcarpalide is a microfilament disrupting agent, and Sch 642305 is an inhibitor of bacterial DNA primase.

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A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2′-alkenyl)- or benzyl-sulfonyl]-benzothiazoles.

Cited by 387 publications

References 22 publications

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

A concise, total synthesis of the TMC-95A/B proteasome inhibitors

Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

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