Abstract
Olefin metathesis is a prevailing method for the construction of organic molecules. Recent advancements in olefin metathesis have focused on stereoselective transformations. Ruthenium olefin metathesis catalysts have had a particularly pronounced impact in the area of stereoselective olefin metathesis. The development of three categories of Z-selective olefin metathesis catalysts has made Z-olefins easily accessible to both laboratory and industrial chemists. Further design enhancements to asymmetric olefin metathesis catalysts have streamlined the construction of complex molecules. The understanding gained in these areas has extended to the employment of ruthenium catalysts to stereoretentive olefin metathesis, the first example of a kinetically E-selective process. These advancements, as well as synthetic applications of the newly developed catalysts, are discussed.
Highlights
The discovery of well-defined ruthenium OM catalysts has opened the door for investigations into the structure-activity relationships of the ligand framework
Further pursuits into the design of stereoselective ruthenium metathesis catalysts have led to interesting discoveries and a much enhanced understanding of the role olefin complexation and the ruthenacyclobutane play in the
Further pursuits into the design of stereoselective ruthenium metathesis catalysts have led to interesting discoveries and a much enhanced understanding of the role olefin complexation and the ruthenacyclobutane play in the setereoselectivity of OM
Summary
[e2+12)][c1y5c].loUapdodnitigoenncearnatoioccnuorf, faomrmeitnagl-caarmbeetnaell,aacnycolloebfiuntacnane,cwhehliacthectaonththeemnectyacllsopreevcieerst., [f2o+rm2]incygcalonaedwditoiloenfincaannodcmcuert,aflo-rcmaribnegnea smpeetcaiellsa.cyclobutane, which can cyclorevert, forming a new olefin and metal-carbene species. GGeenneerraallllyy aacccceepptteedd mmeecchhaanniissmm ffoorr oolleeffiinn mmeettaatthheessiiss ((OOMM)) pprroocceeeeddiinngg tthhrroouugghh aa [[22++22]] cycloaddition followed by cycloreversion to generate a new olefifin. OM research focused on the desymmetrization of achiral olefins to provide chiral molecules through Cthatealayslttse2r0a1t6io, 6n, 8o7f; dthoie:1l0i.g33a9n0d/castcala7f0f3o0l0d87[11,16,17]. Catalysts 2017, 7, 87 stereoselective OM research focused on the desymmetrization of achiral olefins to provide chiral Cmatoallyesctus 2le01s7,t7h, r8o7 ugh the alteration of the ligand scaffold [11,16,17]. As understanding for otfh3e8 stereochemical arrangement of the metallacycle intermediate progressed, further variations were mofatdhee imn ectoanlltaincyucallepinutresrumiteodfiaotneeporfogthreesusendm, efut rcthhaelrlevnagreiastiinonOsMw:ekreinmetaicdeZ-isnelceocntitvinituya[l1p8u–2rs0u].itAonf ionncereodfitbhlee uanmmoeutncthoaflleenffgoerst ihnaOs Mbe: ekninedteicvoZt-esdeletoctitvhietyse[1q8u–e2s0t]s.,Awnhiincchrehdaibvlee oapmeonuendt tohfeefdfoorotrhatos nbeuemnedroeuvsotdeidsctoovtehreiesse. RAeolssoe,lemctuivche pmroolgyrbedssenhuams reacnednttluynbgesetnenmmadeetaitnhethsiesucsaetaolfyssttesr[e1o6s,e1l7e,c2t1iv–2e3m];ohlyobwdeevneur,mthainsdretuvniegwstewnilml feotacuthsesoins rcuattahleynsitusm[1-6b,1a7se,2d1–m2e3t]a; thhoewsiesvceart,atlhyisstsr.eview will focus on ruthenium-based metathesis catalysts
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