Olefin Metathesis Directed to Organic Synthesis: Principles and Applications

2004 ◽  
pp. 223-267 ◽  
Author(s):  
Bernd Schmidt ◽  
Jolanda Hermanns
Keyword(s):  
Organic Synthesis ◽  
Olefin Metathesis

Development of a Hydrazine-Catalyzed Carbonyl-Olefin Metathesis Reaction

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1954-1965 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Double Bond ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Type I ◽  
Type Ii ◽  
Metathesis Reaction ◽  
Alternative Strategies ◽  
Potential Applications ◽  
Acid Catalyzed ◽  
New Strategies

Carbonyl-olefin metathesis is a potentially powerful yet underexplored reaction in organic synthesis. In recent years, however, this situation has begun to change, most notably with the introduction of several different catalytic technologies. The development of one of those new strategies, based on hydrazine catalysts and a novel [3+2] paradigm for double bond metathesis, is discussed herein. First, the stage is set with a description of some potential applications of carbonyl-olefin metathesis and a discussion of alternative strategies for this intriguing reaction.1 Introduction2 Potential Applications of Carbonyl-Olefin Metathesis3 Carbonyl-Olefin Metathesis Strategies4 Direct (Type I): Non-Catalytic5 Direct (Type I): Acid-Catalyzed6 Indirect (Type II): Metal Alkylidenes7 Indirect (Type III): Hydrazine-Catalyzed8 Conclusion

scholarly journals Iodonium-Catalyzed Carbonyl–Olefin Metathesis Reactions

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1966-1970 ◽  
Author(s):  
Giulia Oss ◽  
Thanh Vinh Nguyen
Keyword(s):  
Transition Metal ◽  
Organic Compounds ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Lewis Acids ◽  
Functional Group ◽  
Iodine Monochloride ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Recent Developments

The carbonyl–olefin metathesis reaction has become increasingly important in organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl–olefin metathesis process under mild reaction conditions. This work broadens the scope of this chemical transformation to include iodonium sources as simple and practical catalysts.

Recent advances in olefin metathesis and its application in organic synthesis

Tetrahedron ◽  
1998 ◽  
Vol 54 (18) ◽  
pp. 4413-4450 ◽  
Author(s):  
Robert H. Grubbs ◽  
Sukbok Chang
Keyword(s):  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Recent Advances

Olefin Metathesis Directed to Organic Synthesis: Principles and Applications

ChemInform ◽  
2005 ◽  
Vol 36 (40) ◽  
Author(s):  
Bernd Schmidt ◽  
Jolanda Hermanns
Keyword(s):  
Organic Synthesis ◽  
Olefin Metathesis

scholarly journals The allylic chalcogen effect in olefin metathesis

2010 ◽  
Vol 6 ◽  
pp. 1219-1228 ◽  
Author(s):  
Yuya A Lin ◽  
Benjamin G Davis
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Chemical Biology ◽  
Positive Influence ◽  
Efficient Synthesis ◽  
Cross Metathesis ◽  
Allyl Sulfide ◽  
Hydroxy Groups ◽  
Allyl Sulfides

Olefin metathesis has emerged as a powerful tool in organic synthesis. The activating effect of an allylic hydroxy group in metathesis has been known for more than 10 years, and many organic chemists have taken advantage of this positive influence for efficient synthesis of natural products. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins. This led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology. The enhanced reactivity of allyl sulfide, along with earlier reports of a similar effect by allylic hydroxy groups, suggests that allyl chalcogens generally play an important role in modulating the rate of olefin metathesis. In this review, we discuss the effect of allylic chalcogens in olefin metathesis and highlight its most recent applications in synthetic chemistry and protein modifications.

scholarly journals Aqueous olefin metathesis: recent developments and applications

2019 ◽  
Vol 15 ◽  
pp. 445-468 ◽  
Author(s):  
Valerio Sabatino ◽  
Thomas R Ward
Keyword(s):  
Double Bond ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Chemical Biology ◽  
Polymer Chemistry ◽  
Attractive Alternative ◽  
Bond Forming ◽  
Recent Developments ◽  
Tremendous Impact ◽  
Made In

Olefin metathesis is one of the most powerful C–C double-bond-forming reactions. Metathesis reactions have had a tremendous impact in organic synthesis, enabling a variety of applications in polymer chemistry, drug discovery and chemical biology. Although challenging, the possibility to perform aqueous metatheses has become an attractive alternative, not only because water is a more sustainable medium, but also to exploit biocompatible conditions. This review focuses on the progress made in aqueous olefin metatheses and their applications in chemical biology.

scholarly journals Recent advances in ruthenium-based olefin metathesis

2018 ◽  
Vol 47 (12) ◽  
pp. 4510-4544 ◽  
Author(s):  
O. M. Ogba ◽  
N. C. Warner ◽  
D. J. O’Leary ◽  
R. H. Grubbs
Keyword(s):  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Functional Group ◽  
Polymer Science ◽  
Enabling Technology ◽  
Broad Applicability ◽  
Recent Advances ◽  
Metathesis Catalysts

Ruthenium-based olefin metathesis catalysts, known for their functional group tolerance and broad applicability in organic synthesis and polymer science, continue to evolve as an enabling technology in these areas.

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