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DOI: 10.1055/s-0030-1261235
Asymmetric Synthesis of Novel Biaryl Analogues with a Fused Chiral Bicyclic Bridge Using α-Amino Acids as Chiral Sources
Publication History
Publication Date:
13 September 2011 (online)
Abstract
A series of biaryl anologues with a fused bicyclic bridge were synthesised in a diastereoselectivity of up to 14:86 via an intramolecular cyclisation of an in situ generated N-acyliminium ion. The absolute configuration of products 9b-d and 10b-d was clearly defined by a combination of X-ray crystal-structural analysis, NOE difference, and CD experiments.
Key words
biaryl - diastereoselectivity - cyclisation mechanism - N-acyliminium ion - absolute configuration
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- Supporting Information
- 1
Rosini C.Franzini L.Raffaelli A.Salvadori P. Synthesis 1992, 503 - 2
McCarthy M.Guiry PJ. Tetrahedron 2001, 57: 3809 - 3
Joncour A.Décor A.Liu JM.Tran ME.Dau H.Baudoin O. Chem. Eur. J. 2007, 13: 5450 - 4
Baudoin O.Guénard D.Guéritte F. Mini-Rev. Org. Chem. 2004, 1: 333 - 5
Décor A.Monse B.Martin MT.Chiaroni A.Thoret S.Guénard D.Guéritte F.Baudoin O. Bioorg. Med. Chem. 2006, 14: 2314 - 6
Baudoin O.Claveau F.Thoret S.Herrbach A.Guénard D.Guéritte F. Bioorg. Med. Chem. 2002, 10: 3395 - 7
Pascal C.Dubois J.Guénard D.Guéritte F. J. Org. Chem. 1998, 63: 6414 - 8
Zavala F.Guénard D.Robin JP.Brown E. J. Med. Chem. 1980, 23: 546 - 9
Monovich LG.Huérou YL.Rönn M.Molander GA. J. Am. Chem. Soc. 2000, 122: 52 - 10
Pu L. Chem. Rev. 1998, 98: 2405 - 11
Morita H.Awang K.Hadi AHA.Takeya K.Itokawa H.Kobayashi J. Bioorg. Med. Chem. Lett. 2005, 15: 1045 - 12
Pascal C.Dubois J.Guénard D.Tchertanov L.Thoret S.Guéritte F. Tetrahedron 1998, 54: 14737 - 13
Bringmann G.Mortimer AJP.Keller PA.Gresser MJ.Garner J.Breuning M. Angew. Chem. Int. Ed. 2005, 44: 5384 - 14
Herrbach A.Marinetti A.Baudoin O.Guénard D.Guéritte F. J. Org. Chem. 2003, 68: 4897 - 15
Broady SD.Golden MD.Leonard J.Muir JC.Maudet M. Tetrahedron Lett. 2007, 48: 4627 - 16
Büttner F.Bergemann S.Guénard D.Gust R.Seitz G.Thoret S. Bioorg. Med. Chem. 2005, 13: 3497 - 17
Bergemann S.Brecht R.Büttner F.Guénard D.Gust R.Seitz G.Stubbs MT.Thoret S. Bioorg. Med. Chem. 2003, 11: 1269 - 18
Beryozkina T.Appukkuttan P.Mont N.Eycken EV. Org. Lett. 2006, 8: 487 - 19
Maryanoff BE.Zhang HC.Cohen JH.Turchi IJ.Maryanoff CA. Chem. Rev. 2004, 104: 1431 - 20
Zhao HW.Su S.Cui J.Song XQ.Qin X.Li HL.Yan H.Zhong RG.Hu LM. Synlett 2010, 2557 - 23
Dutot L.Gaucher A.Wright K.Wakselman M.Mazaleyrat JP.Oancea S.Peggion C.Formaggio F.Toniolo C. Tetrahedron: Asymmetry 2006, 17: 363 - 24
Royer J.Bonin M.Micouin L. Chem. Rev. 2004, 104: 2311 - 25
IJzendoorn DR.Botman PNM.Blaauw RH. Org. Lett. 2006, 8: 239 - 26
Speckamp WN.Moolenaar NJ. Tetrahedron 2000, 56: 3817
References and Notes
General Procedure
for the Cyclisations of Compounds 8b-d
To
a well-stirred solution of compound 8b-d (1.0 equiv)in anhyd acetonewas added
TsOH (0.5 equiv) in one portion. The resulting reaction solution
wa s stir red at r.t. for 2-4 h. The reaction solution
was concentrated under reduced pressure, and the crude products
were purified with column chromatography on silica gel to afford 9b-d and 10b-d, individually.
Analytical Data of (2
R
)-9b
Mp 75-77 ˚C; [α]D
²³ -155.5
(c 1.0, CHCl3). ¹H
NMR (400 MHz, CDCl3): δ = 7.89 (dd, J = 7.6, 1.2 Hz, 1 H), 7.72-7.82 (m,
2 H), 7.29-7.49 (m, 5 H), 6.33 (br, 1 H), 4.21 (br, 1 H), 1.82
(br, 3 H), 1.58 (br, 9 H). ¹³C NMR
(100 MHz, CDCl3): δ = 169.1, 154.2,
133.5, 132.1, 130.7, 128.7, 128.7, 127.4, 126.4, 124.1, 123.6, 122.8,
81.6, 70.3, 55.0, 29.6, 28.3, 18.5, 16.9. ESI-HRMS: m/z calcd for C21H23N2O3 [M + H+]: 351.1700;
found: 351.1703. HPLC: t
R = 13.0
min [Chiralpak OD-H (25 cm × 0.46
cm), Daicel Chemical Ind., Ltd., hexane-i-PrOH
(50:1), 1.0 mL/min, >99% ee].
C27H26N2O3, M = 426.52, orthorhombic, a = 9.920 (7), b = 11.644 (3), c = 19.686 (6) Å, V = 2273.9 (18) ų, T = 293 K, space group P212121, Z = 4, 4035 reflections measured, 3686 unique (R int = 0.033) which were used in all calculations. The final R1 = 0.0318 with wR2 = 0.0838. The X-ray crystallographic data of compound (2S,12bS,M)-9d was deposited at the Cambridge Crystallographic Data Centre (CCDC-773497).