{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T13:05:44Z","timestamp":1785848744793,"version":"3.56.0"},"reference-count":112,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2003,11,28]],"date-time":"2003-11-28T00:00:00Z","timestamp":1069977600000},"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":[[2003,12,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The sequential low\u2010temperature addition reaction of an organolithium compound and methyl triflate to (menthyloxy)(3\u2010furyl)carbene complexes of chromium and tungsten proceeded with excellent regioselectivity (1,4\u2010addition) and diastereoselectivity (2,3\u2010<jats:italic>trans<\/jats:italic> disposition of the nucleophile and electrophile groups) to afford new 2,3\u2010disubstituted (2,3\u2010dihydro\u20103\u2010furyl)carbene complexes. In addition, a high degree of diastereofacial selectivity was achieved by employing alkenyllithium compounds. After detachment of both the metal fragment and the chiral auxiliary group, trisubstituted 2,3\u2010dihydrofuran derivatives containing a quaternary stereogenic center at the C3 position were obtained. The characterization, including X\u2010ray crystallography, of a novel type of stable four\u2010membered chelate (\u03b7<jats:sup>2<\/jats:sup>\u2010alkene)tetracarbonylcarbene complex of chromium is also reported.<\/jats:p>","DOI":"10.1002\/chem.200305241","type":"journal-article","created":{"date-parts":[[2003,12,9]],"date-time":"2003-12-09T11:00:37Z","timestamp":1070967637000},"page":"5725-5736","source":"Crossref","is-referenced-by-count":36,"title":["Asymmetric Dearomatization of the Furan Ring Promoted by Conjugate Organolithium Addition to (Menthyloxy)(3\u2010furyl)carbene Complexes of Chromium"],"prefix":"10.1002","volume":"9","author":[{"given":"Jos\u00e9","family":"Barluenga","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sandip K.","family":"Nandy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Y. R. Santosh","family":"Laxmi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Ram\u00f3n","family":"Su\u00e1rez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isabel","family":"Merino","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Josefa","family":"Fl\u00f3rez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Santiago","family":"Garc\u00eda\u2010Granda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9","family":"Montejo\u2010Bernardo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2003,11,28]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961080707"},{"key":"e_1_2_6_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199607291"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9902852"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-008096519-2.00061-8"},{"key":"e_1_2_6_6_2","volume-title":"Heterocyclic Chemistry","author":"Joule J. 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J.","year":"1982","journal-title":"Tetrahedron Lett."},{"key":"e_1_2_6_41_2","unstructured":"In addition reaction of furan with radical species produced a stereoisomeric mixture of 1 4\u2010addition products (2 5\u2010dialkyl\/aryl\u20102 5\u2010dihydrofurans):"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/j29690001253"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)72419-1"},{"key":"e_1_2_6_44_2","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)92456-6"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)94214-X"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00265a035"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)82929-4"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1990-21235"},{"key":"e_1_2_6_50_2","unstructured":"\u00a0"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00091a076"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja972866j"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr940316n"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00805-5"},{"key":"e_1_2_6_55_2","unstructured":"Complexes of the type: [tpRe(CO)(L)(\u03b72\u2010furan)] tp=hydridotris(pyrazolyl)borate L=tBuNC PMe3 pyridine 1\u2010methylimidazole."},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010513l"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja962770"},{"key":"e_1_2_6_58_2","unstructured":"\u00a0"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19771100829"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)87497-3"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00167a038"},{"key":"e_1_2_6_62_2","unstructured":"Crystal data for minor\u20103\u2009a: C24H34CrO6 Mr=470.51 crystal size 0.17\u00d70.15\u00d70.10 mm orthorhombic space groupP212121 a=10.9770(8) b=14.9881(9) c=15.3515(16) \u00c5 V=2525.7(4) \u00c53 \u03c1calcd=1.237 Mg\u2009m\u22123 T=200(2) K. 11\u2009974 reflections were measured 4722 independent and 4167 (I>2\u03c3(I)) with\u03bc=4.007 mm\u22121 Tmin=0.466 andTmax=0.670. All hydrogen atoms were treated by a mixture of independent and constrained refinement. Final conventionalR=0.0417 wR2=0.1019 for 280 parameters refined onF2. Final residual electron density 0.196 and \u22120.298 e\u2009\u00c5\u22123. Absolute configuration Flack parameter 0.009(5)."},{"key":"e_1_2_6_63_2","unstructured":"The size of the chelate ring has been defined by taking the center of the coordinated double bond as one ring member."},{"key":"e_1_2_6_64_2","unstructured":"For related \u03b72\u2010alkene(tetracarbonyl)carbene complexes of Group 6 metals with either a three\u2010 five\u2010 or six\u2010membered chelate structure and which have been characterized by X\u2010ray crystallography see: Cr derivatives:"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19860980920"},{"key":"e_1_2_6_65_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198608121"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00111a024"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00103a058"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(87)80038-4"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)86779-0"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00373a015"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00325a008"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39840000574"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39840000576"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00148a025"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(87)80252-8"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja972880w"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja991865j"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0277-5387(00)86941-7"},{"key":"e_1_2_6_79_2","unstructured":"IntermediateAreacts also with other electrophilic reagents; for example with benzaldehyde a different regioisomer was obtained corresponding to electrophile addition to C5. Further work on this subject is underway."},{"key":"e_1_2_6_80_2","unstructured":"\u00a0"},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00132a031"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(90)87286-M"},{"key":"e_1_2_6_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00017a006"},{"key":"e_1_2_6_84_2","first-page":"31","volume":"8","author":"Allen F. H.","year":"1993","journal-title":"Chemical Design Automation News"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt98900000s1"},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00049a038"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00061a016"},{"key":"e_1_2_6_88_2","unstructured":"In this experiment we also observed a mixture of unidentified products."},{"key":"e_1_2_6_89_2","unstructured":"The scope and limitations of this latter reaction are currently being studied in our laboratory. These results will be reported separately."},{"key":"e_1_2_6_90_2","unstructured":"The NMR spectra measured included1H 13C DEPT gHMQC gHMBC gCOSY and NOESY."},{"key":"e_1_2_6_91_2","unstructured":"Crystal data for minor\u20104\u2009e: C22H30O3 Mr=342.48 crystal size 0.32\u00d70.25\u00d70.25 mm orthorhombic space groupP212121 a=9.3736(1) b=11.0456(2) c=18.6432(3) \u00c5 V=1930.26(5) \u00c53 \u03c1calcd=1.178 Mg\u2009m\u22123 T=200(2) K. 3615 independent and 3339 (I>2\u03c3(I)) \u03bc=0.603 mm\u22121 Tmin=0.817 andTmax=0.865. All hydrogen atoms were treated by a mixture of independent and constrained refinement. Final conventionalR=0.0468 wR2=0.1093 for 307 parameters refined onF\u20092. Final residual electron density 0.262 and \u22120.340 e\u2009\u00c5\u22123. Absolute configuration Flack parameter 0.00(3)."},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01261a013"},{"key":"e_1_2_6_93_2","unstructured":"Prepared from commercially available \u03b2\u2010bromostyrene (E:Z90:10) by bromine\u2013lithium exchange reaction withtBuLi."},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00595-0"},{"key":"e_1_2_6_95_2","unstructured":"Crystal data for12: C24H28O5 Mr=396.49 crystal size 0.40\u00d70.20\u00d70.08 mm monoclinic space groupP21 a=16.4134(3) b=6.1783(1) c=21.1099(4) \u00c5 V=2054.25(6) \u00c53 \u03c1calcd=1.282 Mg\u2009m\u22123 T=120(2) K. 23\u2009416 reflections were measured 7564 independent and 7071 (I>2\u03c3(I)).\u03bc=0.720 mm\u22121 Tmin=0.764 andTmax=0.954. All hydrogen atoms were treated by a mixture of independent and constrained refinement. Final conventionalR=0.0576 wR2=0.1960 for 520 parameters refined onF\u20092. Final residual electron density 0.417 and \u22120.401 e\u2009\u00c5\u22123. Absolute configuration Flack parameter \u22120.2(2)."},{"key":"e_1_2_6_96_2","unstructured":"Indeed the analogous reaction of methoxycarbene complex7with (E)\u20102\u2010phenylethenyllithium afforded only pentacarbonylcarbene complex13with mainly atransconfiguration of the exocyclic C\uf8feC bond. The observed 7:1 mixture ofE:Zisomers of13is close to theE:Zmixture of the starting \u03b2\u2010bromostyrene."},{"key":"e_1_2_6_97_2","unstructured":"A competing intramolecular displacement by one of the \u03c0 systems of a CO ligand at the level of intermediateD which will certainly reduce the steric strain could account for the finally observed 1:1 ratio ofE:Zisomers."},{"key":"e_1_2_6_98_2","unstructured":"For other recent asymmetric synthesis of 2 3\u2010dihydrofurans see:"},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960581l"},{"key":"e_1_2_6_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011983i"},{"key":"e_1_2_6_101_2","first-page":"286","volume":"8","author":"Gilman H.","year":"1954","journal-title":"Org. 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