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Alkene Metathesis in Organic Synthesis (Topics in by Alois Fuerstner

By Alois Fuerstner

The great development in olefin metathesis completed over the last decade can not often be overvalued. as a result of improvement of a brand new new release of good outlined and high-performance organometallic catalysts, this response is swiftly evolving into probably the most flexible instruments for complex natural chemistry, ordinary product synthesis, wonderful chemical creation and polymer sciences. Written via a number of the major specialists during this box, this monograph intends to familiarize the reader with the main fascinating advancements and frontiers during this flourishing box of chemistry study.

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Substrate Product Yield 1d 24 1 93% [100%] 2 97% [100%] 3 96% [100%] 4 [25%] 96% 5 97% [100%] a Isolated yield [yield determined by NMR]. 48 A. Fürstner Table 2. continued No. Substrate Product Yield 1d 24 6 0% 93% 7 0% 61% 8 98% [100%] 9 0% 96% 10 [25%] 97% 11 [5%] 89% 12 0% 0% 13 98% decomp. 14 97% [100%] a Isolated yield [yield determined by NMR]. Ruthenium-Catalyzed Metathesis Reactions in Organic Synthesis 49 Scheme 9. Scheme 10. tries 6, 7), the best substrates for reactions with 1 and 2 are terminal, monosubstituted olefins.

The idea of determining the site of initiation via the substitution pattern of the olefin has also been used by Blechert et al. during the course of a stereocontrolled RCM process (Scheme 10). Again, the reaction starts most likely at the terminal olefin site in 33 independent of whether 1 or 24 is used as catalyst; however, due to the different coordination geometries of ruthenium and molybdenum, the evolving carbene reacts with either diastereotopic olefin attached to 50 A. Fürstner Scheme 11. the nitrogen substituent, thus leading to the selective formation of 34 or 35, respectively (Scheme 10) [21].

E. the smaller and more electron-withdrawing chloride leads to the most active species. As mentioned above, the initiation period is shorter if the substituent on the carbene moiety is R1=C6H4Y rather than R1= CH=CPh2; however, electronic effects of the substituent Y on the phenyl ring turned out to be of minor importance (Y=H, NMe2, OMe, Me, F, Cl, NO2). Further variations of the basic motif of 1 comprise carbene 1e in which the anionic ligands are trifluoroacetate rather than chloride (Fig. 2) [4d].

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