9.4, 7.6 Hz, C(2)HA), 2.83 (1H, dd, J 9.4, 7.3 Hz, C(2)HB), 3.32
(1H, dd, J 11.8, 1.7 Hz, C(4)CHB), 3.54 (1H, q, J 7.5 Hz, C(3)H),
3.61 (2H, s, NCH2Ph), 3.99 (2H, s, NCH2Ph), 4.08 (1H, q, J
6.8 Hz, C(a)H), 7.10–7.62 (20H, m, Ph); dC (100 MHz, CDCl3)
13.6, 36.2, 44.4, 53.1, 56.0, 56.6, 58.7, 59.3, 60.8, 125.7, 126.7,
126.9, 128.0, 128.1, 128.3, 128.4, 128.6, 128.9, 139.4, 141.3, 142.5,
Gasse, M. Vidal, C. Garbay and H. Galons, Tetrahedron Lett., 2004,
45, 3603.
11 S. G. Davies, N. M. Garrido, D. Kruchinin, O. Ichihara, L. J. Kotchie,
P. D. Price, A. J. Price Mortimer, A. J. Russell and A. D. Smith,
Tetrahedron: Asymmetry, 2006, 17, 1793.
12 S. Bailey, S. G. Davies, A. D. Smith and J. M. Withey, Chem. Commun.,
2002, 2910; S. G. Davies, D. D´ıez, M. M. El Hammouni, A. C. Garner,
N. M. Garrido, M. J. C. Long, R. M. Morrison, A. D. Smith, M. J. Sweet
and J. M. Withey, Chem. Commun., 2003, 2410; S. G. Davies, M. E.
Bunnage, A. M. Chippendale, R. M. Parkin, A. D. Smith and J. M.
Withey, Org. Biomol. Chem., 2003, 1, 3698; S. G. Davies, M. E. Bunnage,
R. M. Parkin, P. M. Roberts, A. D. Smith and J. M. Withey, Org. Biomol.
Chem., 2004, 2, 3337; S. G. Davies, A. C. Garner, M. J. C. Long, A. D.
Smith, M. J. Sweet and J. M. Withey, Org. Biomol. Chem., 2004, 2,
3355; S. G. Davies, A. C. Garner, M. J. C. Long, R. M. Morrison,
P. M. Roberts, A. D. Smith, M. J. Sweet and J. M. Withey, Org. Biomol.
Chem., 2005, 3, 2762.
13 For selected recent examples see: S. G. Davies, R. J. Kelly and A. J. Price
Mortimer, Chem. Commun., 2003, 2132; S. G. Davies, A. J. Burke, A. C.
Garner, T. D. McCarthy, P. M. Roberts, A. D. Smith, H. Rodriguez-
Solla and R. J. Vickers, Org. Biomol. Chem., 2004, 2, 1387; S. G. Davies,
D. G. Hughes, R. L. Nicholson, A. D. Smith and A. J. Wright, Org.
Biomol. Chem., 2004, 2, 1549; S. G. Davies, J. R. Haggitt, O. Ichihara,
R. J. Kelly, M. A. Leech, A. J. Price Mortimer, P. M. Roberts and A. D.
Smith, Org. Biomol. Chem., 2004, 2, 2630.
143.8; m/z (CI+) 461 ([M + H]+, 100%); HRMS (CI+) C33H37N2
+
([M + H]+) requires 461.2957; found 461.2957.
(3R,4R)-3-Amino-4-benzylpyrrolidine 41. Pd(OH)2/C (140 mg,
50% w/w), 38 (280 mg, 0.61 mmol) in MeOH (5 mL) and H2
(5 atm) were reacted according to general procedure 5. Chromatog-
raphy (basic alumina, eluent MeOH) gave 41 as a colourless oil
(103 mg, 64%); [a]2D2 −39.1 (c 1.1 in CHCl3); mmax (film) 3358, 2928,
1495; dH (400 MHz, d4-MeOH) 2.53–2.66 (1H, m, C(4)H), 2.69
(1H, dd, J 11.5, 3.8 Hz, C(4)CHA), 2.93 (1H, dd, J 11.5, 7.6 Hz,
C(4)CHB), 3.16–3.23 (3H, m, C(2)HA, C(5)H2), 3.40 (1H, dd, J
12.1, 6.8 Hz, C(2)HB), 3.62–3.65 (1H, m, C(3)H), 4.89 (1H, br s,
NH2), 7.16–7.34 (5H, m, Ph); dC (100 MHz, d4-MeOH) 33.6, 44.9,
48.9, 52.3, 52.7, 126.6, 128.7, 128.8, 139.8; m/z (CI+) 177 ([M +
H]+, 100%); HRMS (CI+) C11H17N2+ ([M + H]+) requires 177.1392;
found 177.1393.
14 S. G. Davies and G. D. Smyth, Tetrahedron: Asymmetry, 1996, 7, 1005;
S. G. Davies and G. D. Smyth, J. Chem. Soc., Perkin Trans. 1, 1996,
2467; S. G. Davies, A. C. Garner, R. L. Nicholson, J. Osborne, E. D.
Savory and A. D. Smith, Chem. Commun., 2003, 2134.
15 S. G. Davies, A. D. Smith and P. D. Price, Tetrahedron: Asymmetry,
2005, 16, 2833.
16 S. G. Davies, A. C. Garner, E. C. Goddard, D. Kruchinin, P. M. Roberts,
H. Rodriguez-Solla and A. D. Smith, Chem. Commun., 2006, 2664.
17 N-Benzyl-2-oxopyrrolid-3-enone 2 was prepared according to the
procedure of: G. Vo-Thanh, V. Boucard, H. Sauriat-Dorizon and F.
Guibe, Synlett, 2001, 37.
18 N. Asao, T. Uyehara and Y. Yamamoto, Tetrahedron, 1990, 46, 4563;
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19 S. D. Bull, S. G. Davies and A. D. Smith, Tetrahedron: Asymmetry, 2001,
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1284.
20 The absolute configuration of (3R,aS)-5 was assigned by analogy
with the model previously developed to explain the stereoselectiv-
ity observed during addition of homochiral lithium N-benzyl-N-(a-
methylbenzyl)amide to a,b-unsaturated esters; see: J. F. Costello, S. G.
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21 F. Garro-Helion, A. Merzouk and G. Guibe´, J. Org. Chem., 1993, 58,
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22 B. C. Laguzza and B. Ganem, Tetrahedron Lett., 1981, 22, 1483.
23 J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34,
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24 A. E. Shchekotikhin, V. A. Glazunova, Y. N. Luzikov, V. N. Buyanov,
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Chem., 2006, 14, 5241.
25 (S)-N(1)-tert-Butoxycarbonyl-3-aminopyrrolidine 11 is commercially
available from the Aldrich Chemical Company.
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