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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 9
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Original Articles

The Synthesis of Chiral Hmpa Analogues

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Pages 657-663 | Published online: 05 Dec 2006

References

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  • Milwaukee, WI : Aldrich Chemical Company, Inc. .
  • Seebach , D. , Kalinowski , H. , Bastani , B. , Crass , G. , Daum , H. , Dorr , H. , DuPreez , N. P. , Ehrig , V. , Langer , W. , Nussler , C. , Oei , H. and Schmidt , M. 1977 . Helv. Chim. Acta , 60 : 301
  • Guttman , S. 1961 . Helv. Chim. Acta , 44 : 721
  • Compound 10: Bp = 143–50 @ 0.9 mm, mp = 44–48°C NMR) CDCl3). 1.67–2.20 (8H—m), 3.00–3.57 (8H, m). CMR (CDCl3), SFORD 25.90 (d, JPC=9.28 Hz), 46.88 (d, JPC=3.39 Hz) MS m/e (%), 224 (2), 223 (3), 222 (6), 221 (5), 187 (6), 152 (11), 110 (9), 70 (100).
  • Compound 4: NMR (CDCl3), 81.67–2.07 (m, 12H) 0, 2.90–3.53 (m, 12H) 3.38 (s, 3H) 3.70–4.00 (m, 1H). IR (film) 1200, 1075, 1010cm−1 MS m/e (%) No M+, 256 (39), 188 (10), 187 (100), 116 (10), 70 (59), 45 (68) MS-CI 302 (M+1), 270, 256, 93 Bpt 157°/0.04mm Hygroscopic 13C NMR (CDCl3, SFORD) 24.62 (d, JPC = 7.50 Hz), 25.87 (d, JPC=7.72 Hz), 28.49 (d, JPC=6.82 Hz), 45.74 (m), 46.37 (d, JPC=3.4 Hz), 56.70 (d, JPC=4.8 Hz), 58.24
  • Compound 2: NMR (CDCl3) 1.62–2.13 (m, 12H), 2.90–3.55m (10H), 3.72 (s, 3H), 4.12–4.48 (m, 1H) IR (film) 1725, 1200, 1100 cm−1 MS m/e (%) 315 (21), 257 (8), 256 (56), 188 (9), 187 (100), 148 (12), 116 (10), 70 (51) Bpt 193–194o/0.7mm 13C NMR (CDCl3, SFORD) 25.14 (d, JPC=6.71 Hz), 26.05 (d, JPC=7.72 Hz), 30.92 (d, JPC=6.67 Hz), 45.91 (d, JPC=3.95 Hz), 46.40 (d, JPC=3.7 Hz), 51, 34, 59.40 (d, JPC=5.8 Hz), 174. 85
  • Compound 3: NMR (CDCl3) 1.55–2.23 (m, 12H), 2.96–3.43 (m, 10H), 3.43–3.67 (m, 2H), 3.57–4.03 (m, 1H), 6.03 (brs, 1H).
  • Shinkai , S. , Nakaji , T. , Ogawa , T. , Shigematsa , K. and Manabe , O. 1981 . J. Amer. Chem. Soc. , 103 : 111
  • Brown , C. A. and Yamaichi , A. 1979 . J. Chem. Soc. Chem. Commun. , : 100
  • Matrir , W. , Alegria , A. E. and Stevenson , G. R. 1976 . J. Amer. Chem. Soc. , 98 : 7955
  • Jackman , L. M. and Lange , B. C. 1981 . J. Amer. Chem. Soc. , 103 : 4494

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