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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 18-19
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Original Articles

Stereoselective Syntheses of Bridgehead Hydroxy Compounds via Reductive Cyclization Reactions Promoted by Samarium Diiodide

Yung-Son Hon Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan, 11529, R. O. C.
,
Ling Lu Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan, 11529, R. O. C.
&
Kuan-Po Chu Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan, 11529, R. O. C.
Pages 1981-1988 | Accepted 12 Jun 1991, Published online: 23 Sep 2006

References

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  • The spectroscopic data for the cyclized compounds in this work are: Compound 2a white solid (m.p.=48–49.5°C); 1H NMR (CDCl3) δ 1.00–2.24 (m, 12H), 2.52 (dq, J=16.3 and 5.4Hz, 2H, CH2═C═O), 2.91 (s,1H, O═H), 3.69 (s,3H, O═CH3); 13C NMR (CDCl3) δ 19.06, 30.90, 32.91. 33.27, 34.85, 42.70, 46.76, 51.60 (OCH3), 77.88 (C−OH), 174.88 (C═O); IR (CH2Cl2) vmax (cm-1): 3414 (br, OH), 1734 (C═O); MS (m/z): 198 (M+)s, 180, 167, 155 (base peak), 150; Anal. Calcd for C11H18O3:C, 66.60; H, 9.15. Found: C, 66.57; H, 9.44
  • Compound 2b colorless oil; 1H NMR (CDCl3) δ 1.11–2.60 (m, 12H), 3.27 (d, J=6.9 Hz, 2H, CH2C═O), 3.60 (s, 1H, O-H), 7.43–7.58 (m, 3H, Ph-H), 7.97–8.02 (m, 2H, Ph-H); 13C NMR (CDCl3) δ 19.35, 31.08, 33.33, 35.36, 38.21, 42.37, 47.07, 77.94 (C-OH), 128.09, 128.50, 133.15, 136.90, 201.88 (C═O); IR (neat) vmax (cm-1): 3405 (−OH), 1677 (C═O); MS (m/z): 244 (M+), 226, 213, 201, 183, 171, 146, 124, 105 (base peak), 97, 81, 69, 57; HRMS (m/z): 244.1456 (M+, C16H20O2, calcd 244.1412). Compound 4a colorless oil; 1H NMR (CDCl3) δ 0.96–2.45 (m, 10H), 2.50 (dq, J=15.0 and 6.9 Hz, 2H, CH2C═O), 3.15 (br s, 1H, O-H), 3.69 (s, 3H, O-CH3); 13C NMR (CDCl3) δ 28.59, 30.43, 33.67, 35.51, 37.82, 39.91, 45.47, 51.84 (O-CH3), 83.62 (C-OH), 175.10 (C═O); IR (neat) vmax (cm-1): 3419 (O═H), 1738 (C═O); MS (m/z): 184 (M+), 169, 168, 155, 152, 123, 110, 83. Compound 4b colorless oil; 1H NMR (CDCl3) δ 1.00–2.50 (m, 10H), 3.23 (d, J=6.7 Hz, 2H), 3.71 (br s, 1H, O-H), 7.47–7.59 (m, 3H, Ph-H), 7.98–8.02 (m, 2H, Ph-H); 13C NMR (CDCl3) δ 28.82, 30.40, 33.76, 38.26, 39.36, 40.65, 45.53, 63.08, 79.84 (C-OH), 128.14, 128.52, 131.18, 133.23, 201.56 (C═O); IR (neat) vmax (cm-1): 3406 (−OH), 1678 (C═O); MS (m/z): 230 (M+), 212, 201, 184, 157, 146, 133, 125, 110, 105 (base peak), 95, 83, 71; HRMS (m/z): 230.1303 (M+, C15H18O2, calcd 230.1306). Compound 6a colorless oil; 1H NMR (CDCl3) δ 1.26–1.90 (m, 17H), 2.21–2.38 (m, 1H), 2.50 (dq, J=16.2 and 5.4 Hz, 2H, CH2C═O), 2.94 (br, 1H, O-H), 3.68 (s, 3H, O-CH3); 13C NMR (CDCl3) δ 23.57, 26.48, 26.71, 28.97, 31.77, 33.52, 38.90, 42.11, 45.08, 51.65, 79.12 (C-OH), 174.86 (C═O); IR (neat) vmax (cm-1): 3407 (O-H), 1736 (C═O); MS (m/z): 252 (M+), 220, 201, 181, 167, 151 (base peak), 135, 113, 95, 83, 71, 57; HRMS (m/z): 252.1720 (M+, C15H24O3, calcd 252.1725). Compound 6b colorless oil; 1H NMR (CDCl3) δ 1.17–2.04 (m, 16H), 2.40–2.60 (m, 2H), 3.24 (d, J=7.2 Hz, 2H), 3.50 (br, 1H, O-H), 7.43–7.58 (m, 3H, Ph-H), 7.97–8.01 (m, 2H, Ph-H); 13C NMR (CDCl3) δ 24.46, 27.57, 29.88, 32.99, 39.55, 39.78, 42.49, 43.48, 43.90, 44.89, 46.07, 79.05 (C-OH), 128.97, 129.37, 134.02, 137.57, 202.49 (C═O); IR (neat) vmax (cm-1): 34.47 (O-H), 1675 (C═O); MS (m/z): 298(M+), 280, 255, 227, 193, 151, 120, 105; HRMS (m/z): 298.1925 (M+, C20H26O2, calcd 298.1932). Compound 8a colorless oil; 1H NMR (CDCl3) δ 1.15 (s, 3H, C-CH3), 1.24 (m, 1H), 1.55–1.78 (br m, 4H), 1.90–2.10 (m, 1H), 2.21–2.50 (m, 1H), 2.40 (dq, J=11.5 and 7.7 Hz, 2H, CH2C═O), 2.64 (br s, 1H, O-H), 3.69 (s, 3H, O-CH3); 13C NMR (CDCl3) δ 20.38, 22.93, 30.24, 34.90, 41.00, 46.31, 51.65 (O-CH3), 79.26 (C-OH), 174.55 (C═O); IR (neat) vmax (cm-1): 3476 (O═H), 1728 (C═O); MS (m/z): 171 (M+-1), 149, 129, 116 (base peak), 97, 83, 71. Compound 8b colorless oil; 1H NMR (CDCl3) δ 1.22 (s, 3H, C-CH3), 1.30–2.02 (m, 6H), 2.38–2.54 (m, 1H), 3.10 (d, J=6.8 Hz, 2H, CH2C═O), 3.43 (br s, 1H, O-H), 7.47–7.62 (m, 3H, Ph-H), 7.96–8.01 (m, 2H, Ph═H); 13C NMR (CDCl3) δ 21.08, 23.59, 30.97, 39.87, 41.41, 46.13, 79.05 (C-OH), 128.07, 128.52, 133.46, 136.71, 201.32 (C═O); IR (neat) vmax (cm-1): 3467 (O-H), 1675 (C═O); MS (m/z): 218 (M+), 200, 185, 157, 146, 133, 120, 113, 105 (base peak), 93, 81, 71; HRMS (m/z): 218.1304 (M+, C14H18O2, calcd 218.1306)
  • Girard , P. , Namy , J. L. and Kagan , K. B. 1980 . J. Am. Chem. Soc. , 102 : 2693

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