{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T16:18:49Z","timestamp":1791044329156,"version":"4.1.0"},"reference-count":87,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2005,2,1]],"date-time":"2005-02-01T00:00:00Z","timestamp":1107216000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2005,4,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The trimethylsilyl\u2010protected enynes <jats:bold>9\u2009a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> and <jats:bold>14\u2009a<\/jats:bold>,\u2009<jats:bold>b<\/jats:bold> with alkynyl substituents on the three\u2010membered ring or on the double bond of a methylenecyclopropane or a bicyclopropylidene moiety were prepared in two steps from the alcohols <jats:bold>6\u2009a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> and <jats:bold>12\u2009a<\/jats:bold>,\u2009<jats:bold>b<\/jats:bold>, respectively, by conversion to the iodides and their coupling with lithium (trimethylsilyl)acetylide (<jats:bold>8<\/jats:bold>) in 38\u201373\u2009% overall yields. The bicyclopropylidene derivative <jats:bold>9\u2009d<\/jats:bold> was synthesized in 49\u2009% yield directly from bicyclopropylidene (<jats:bold>3<\/jats:bold>) by lithiation followed by coupling with (5\u2010iodopent\u20101\u2010ynyl)trimethylsilane (<jats:bold>11<\/jats:bold>). Enynes <jats:bold>9\u2009b<\/jats:bold>\u2013<jats:bold>d<\/jats:bold> were protiodesilylated by treatment with K<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub> in methanol to give the corresponding unprotected enynes <jats:bold>10\u2009b<\/jats:bold>\u2013<jats:bold>d<\/jats:bold> in 53, 74 and 94\u2009% yield, respectively. Enynes <jats:bold>17\u2009a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> with a carbonyl group adjacent to the acetylenic moiety were synthesized from oxo derivatives <jats:bold>15\u2009a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> by Wittig olefination followed by coupling with <jats:bold>8<\/jats:bold> in 47, 18 and 12\u2009% overall yield, respectively. Pauson\u2013Khand reactions of the methylenecyclopropane derivatives with a substituent on the ring (<jats:bold>9\u2009a<\/jats:bold>,<jats:bold>b<\/jats:bold> and <jats:bold>10\u2009a<\/jats:bold>) as well as on the double bond (<jats:bold>14\u2009a<\/jats:bold>,<jats:bold>b<\/jats:bold> and their in situ prepared protiodesilylated analogues) proceeded smoothly by stirring of the corresponding enyne with [Co<jats:sub>2<\/jats:sub>(CO)<jats:sub>8<\/jats:sub>] in dichloromethane at ambient temperature followed by treatment of the formed complexes with trimethylamine <jats:italic>N<\/jats:italic>\u2010oxide under an oxygen atmosphere at \u221278\u2009\u00b0C to give tricyclic or spirocyclopropanated bicyclic enones <jats:bold>18\u2009a<\/jats:bold>,\u2009<jats:bold>b<\/jats:bold>, <jats:bold>19\u2009a<\/jats:bold>, <jats:bold>20\u2009a<\/jats:bold>,\u2009<jats:bold>b<\/jats:bold>, <jats:bold>21\u2009a,\u2009b<\/jats:bold> in good yields. Alkynylbicyclopropylidene derivatives <jats:bold>9\u2009c<\/jats:bold>,\u2009<jats:bold>d<\/jats:bold> and <jats:bold>10\u2009c<\/jats:bold>,\u2009<jats:bold>d<\/jats:bold> formed the corresponding cobalt complexes at \u221278 to \u221220\u2009\u00b0C. Treatment of the latter with <jats:italic>N<\/jats:italic>\u2010methylmorpholine <jats:italic>N<\/jats:italic>\u2010oxide under an argon atmosphere at \u221220\u2009\u00b0C gave the spirocyclopropanated tricyclic enones <jats:bold>18\u2009c<\/jats:bold>, <jats:bold>19\u2009c<\/jats:bold> and <jats:bold>18\u2009d<\/jats:bold> in 31\u201345\u2009% yields. The structure of <jats:bold>19\u2009c<\/jats:bold> was proved by X\u2010ray crystal structure analysis. The cyclization of enynones <jats:bold>17\u2009a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> in MeCN at 80\u2009\u00b0C gave the spirocyclopropanated bicyclic diketones <jats:bold>22\u2009a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> in 38\u201365\u2009% yields. Intramolecular PKRs of the enynes <jats:bold>25\u2009a<\/jats:bold>,\u2009<jats:bold>d<\/jats:bold> with a chiral auxiliary adjacent to the triple bond gave the corresponding products <jats:bold>26\u2009a<\/jats:bold>,\u2009<jats:bold>d<\/jats:bold> in 70 and 79\u2009% yield, respectively, as 5:1 and 8:1 mixtures of diastereomers, respectively. Addition of lithium dimethylcuprate or higher order cuprates to the double bond of the former furnished bridgehead\u2010substituted bicyclo[3.3.0]octanones <jats:bold>27\u2009a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> in 57\u201386% yields. Protiodesilylation of <jats:bold>27\u2009a<\/jats:bold> followed by acetal cleavage gave the enantiomerically pure spirocyclopropanated bicyclo[3.3.0]octanedione (1<jats:italic>R<\/jats:italic>,5<jats:italic>R<\/jats:italic>)\u2010 <jats:bold>29\u2009a<\/jats:bold> with [<jats:italic>\u03b1<\/jats:italic>]<jats:styled-content>${{{20\\hfill \\atop {\\rm D}\\hfill}}}$<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/tex2gif-ueqn-1.gif\" xlink:title=\"equation image\"\/><\/jats:styled-content>=\u2212148 (<jats:italic>c<\/jats:italic>=1.0 in CHCl<jats:sub>3<\/jats:sub>) in 55\u2009% overall yield.<\/jats:p>","DOI":"10.1002\/chem.200400997","type":"journal-article","created":{"date-parts":[[2005,2,1]],"date-time":"2005-02-01T03:49:48Z","timestamp":1107229788000},"page":"2471-2482","source":"Crossref","is-referenced-by-count":29,"title":["Intramolecular Pauson\u2013Khand Reactions of Methylenecyclopropane and Bicyclopropylidene Derivatives as an Approach to Spiro(cyclopropanebicyclo[<i>n<\/i>.3.0]alkenones)"],"prefix":"10.1002","volume":"11","author":[{"given":"Armin","family":"de Meijere","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Heike","family":"Becker","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andreas","family":"Stolle","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sergei I.","family":"Kozhushkov","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M. 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Stolle Dissertation Universit\u00e4t Hamburg 1992."},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0255126"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00055a013"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00959a053"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(73)80096-1"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1991-20681"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)98052-3"},{"key":"e_1_2_6_73_2","unstructured":"Crystals of compounds19\u2009c 26\u2009dand27\u2009bwere obtained by slow evaporation of their solutions in petroleum ether. The X\u2010ray single crystal data were collected at 153(2) K on a Bruker STOE AED2 diffractometer (MoK\u03b1 graphite monochromator \u03c9scan). The structure was solved by direct methods and refined by full\u2010matrix least squares onF\u20092for all data with the Bruker SHELXTL program suite. Non\u2010hydrogen atoms were refined with anisotropic displacement parameters H atoms were refined isotropically. Crystal data for19\u2009c: C11H12O (160.21) crystal size 0.90\u00d70.80\u00d70.50 mm3 T=153(2) K monoclinic Z=4 space groupP21\/n F(000)=344 a=8.3120(10) b=11.764(2) c=8.7500(10) \u00c5 \u03b1=\u03b3=90 \u03b2=96.090(10)\u00b0 V=850.8(2) \u00c53 \u03c1=1.251 g\u2009cm\u22123 \u03bc=0.078 mm\u22121 intensities measured: 1602 (2\u03b8max=45.82\u00b0) independent: 1469 (Rint=0.0547) 109 parameters refined R1=0.0623 wR2=0.1531 for 1468 reflections withI> 2\u03c3(Io) R1(all data)=0.0833 wR2(all data)=0.1774 GOF=1.062 maximum and minimum residual electron density 0.616 and \u22120.278 e\u2009\u00c5\u22123. Crystal data for26\u2009d: C28H32O3Si (444.63) crystal size 0.60\u00d70.50\u00d70.50 mm3 T=193(2) K orthorhombic Z=4 space groupP212121 F(000)=952 a=9.881(5) b=10.558(4) c=24.100(14) \u00c5 \u03b1=\u03b3=\u03b2=90\u00b0 V=2514(2) \u00c53 \u03c1=1.175 g\u2009cm\u22123 \u03bc=0.119 mm\u22121 intensities measured: 3793 (2\u03b8max=44.98\u00b0) independent: 3281 (Rint=0.0387) 292 parameters refined R1=0.0400 wR2=0.1027 for 3279 reflections withI> 2\u03c3(Io) R1(all data)=0.0413 wR2(all data)=0.1045 GOF=1.041 maximum and minimum residual electron density 0.143 and \u22120.219 e\u2009\u00c5\u22123. Crystal data for27\u2009b: C31H40O3Si (488.72) crystal size 0.50\u00d70.20\u00d70.20 mm3 T=193(2) K monoclinic Z=2 space groupP21 F(000)=528 a=9.630(2) b=8.680(2) c=16.530(3) \u00c5 \u03b1=\u03b3=90 \u03b2=93.30(3)\u00b0 V=1379.4(5) \u00c53 \u03c1=1.177 g\u2009cm\u22123 \u03bc=0.144 mm\u22121 intensities measured: 2315 (2\u03b8max=46.02\u00b0) independent: 2258 (Rint=0.1940) 320 parameters refined R1=0.0717 wR2=0.1609 for 2258 reflections withI> 2\u03c3(Io) R1(all data)=0.1051 wR2(all data)=0.1609 GOF=1.132 maximum and minimum residual electron density 0.638 and \u22120.260 e\u2009\u00c5\u22123. The X\u2010ray crystal structure analysis of the latter compound does establish its stereochemistry but the unsatisfactory highRvalues do permit neither to discuss any structural peculiarities in27\u2009bnor to save the results of this measurements in the Cambridge Crystallographic Data Centre. CCDC\u2010252\u2009041 (19\u2009c) and \u2010252\u2009040 (26\u2009d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/data_request\/cif"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00059a009"},{"key":"e_1_2_6_75_2","unstructured":"\u00a0"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)91425-5"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)94968-2"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00282a036"},{"key":"e_1_2_6_79_2","unstructured":"H. Becker Dissertation Universit\u00e4t G\u00f6ttingen 1996. The preparation of compound17\u2009dis also mentioned in ref. [10e]."},{"key":"e_1_2_6_80_2","unstructured":"The corresponding desilylated compounds gave only low yields of bicyclic products in the PKRs with almost no diastereoselectivity independent of whatever protocol was used."},{"key":"e_1_2_6_81_2","unstructured":"These values are somewhat lower than those obtained by repetition of our results but with 2 5\u2010dimethoxy\u20102 5\u2010dimethylhexane\u20103 4\u2010diol as an auxiliary for which diastereoselection in the range of 1:10 to 1:20 has recently been reported; see ref. 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