Transition-metal-catalyzed rearrangement of 1,1-(Oligomethylene)-4-aryl-2- butene-1,4-diols: Ring expansion vs. aryl group migration

Synlett

Volumn , Issue 18, 2009, Pages 2987-2991

  Lange, Alex ^a   Heydenreuter, Wolfgang ^a   Menz, Helge ^a   Kirsch, Stefan F ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alkenes; Catalysis; Diols; Rearrangements; Transition metals

Indexed keywords

ALKENE; CYCLOHEXANONE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ISOMERIZATION; MIGRATION; REACTION ANALYSIS; SYNTHESIS;

EID: 72049123761     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218274     Document Type: Article

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55. Synthesis of (E)-2-(4-Methoxystyryl)cyclohexanone (2b)Cu(OTf)2 (1 mg, 0.003 mmol, 1 mol%) was added to a solution of (E)-1-(4-methoxyphenyl)-3-(1- (triethylsilyloxy) cyclopentyl)prop-2-en-1-ol (1c, 100 mg, 0.28 mmol) in CH2Cl2 (2.8 mL) and stirred at r.t. for 30 min (until TLC analysis indicated complete conversion). The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica (pentanes-Et2O = 95:5). Compound 2b was obtained as acolorless solid in 96% yield (62 mg, 0.27 mmol). 1H NMR (360 MHz, CDCl3): d = 1.69-1.83 (m, 3 H), 1.89-1.96 (m, 1H), 2.01-2.09 (m, 1 H), 2.14-2.20 (m, 1 H), 2.31-2.40 (m, 1H), 2.45-2.51 (m, 1 H), 3.17 (ddd, J = 0.9, 6.4, 11.3 Hz, 1H), 3.80 (s, 3 H), 6.27 (dd, J = 5.9, 16.1 Hz, 1 H), 6.33 (d,J = 16.1 Hz, 1 H), 6.77-6.91 (m, 2 H), 7.29-7.33 (m, 2 H).13C NMR (90.6 MHz, CDCl3): d = 24.4 (t), 27.6 (t), 34.5 (t),41.7 (t), 54.0 (d), 55.3 (d), 113.9 (d), 125.3 (d), 127.4 (d),130.0 (s), 130.8 (d), 159.0 (s), 211.3 (s). LRMS (EI): m/z =230 (100)[M+], 202 (26), 173 (25), 159 (21), 134 (38), 121(37). HRMS: m/z calcd for C15H18O2 [M+]: 230.1307; found:230.1307
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58. We also observed a high-yielding elimination when using 2-butene-1,4-diols that possess Bz-protected primary allylic alcohols. According to preliminary studies, this elimination appears to be quite general (Scheme 7).
59. In seminal studies on related 1,3-isomerizations of phenylpropenyl carbinols, chirality transfer was reported
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62. This correlates with the migratory aptitude observed in Wagner-Meerwein shifts