References
1a
Mohr P.
Waespe-Sarcevic N.
Tamm C.
Gawronska K.
Gawronski JK.
Helv. Chim. Acta
1983,
66:
2501
1b
Walser P.
Renold P.
N’Goka V.
Hosseinzadeh F.
Tamm C.
Helv.
Chim. Acta
1991,
74:
1941
1c
Schneider M.
Engel N.
Hönicke P.
Heinemann G.
Görisch H.
Angew.
Chem., Int. Ed. Engl.
1984,
23:
67
2a
Mosbach K.
FEBS Lett.
1976,
62:
E80
2b
Worsfold P.
Pure
Appl. Chem.
1995,
67:
597
For recent reviews see:
3a
Ley SV.
Baxendale IR.
Bream RN.
Jackson PS.
Leach AG.
Longbottom DA.
Nesi M.
Scott JS.
Storer RI.
Taylor SJ.
J. Chem. Soc., Perkin Trans. 1
2000,
3815
3b
Kirschning A.
Monenschein H.
Wittenberg R.
Angew.
Chem. Int. Ed.
2001,
40:
650
3c
Guino M.
Brule E.
De Miguel YR.
Chimica
Oggi-Chem. Today
2002,
20:
23
3d
Ley SV.
Baxendale IR.
Brusotti G.
Caldarelli M.
Massi A.
Nesi M.
Farmaco
2002,
57:
321
4a
Allan RD.
Curtis DR.
Headley PM.
Johnston GAR.
Lodge D.
Twitchin BJ.
J. Neurochem.
1980,
34:
652
4b
Kusama T.
Spivak CE.
Whiting P.
Dawson VL.
Schaeffer JC.
Uhl GR.
Br.
J. Pharmacol.
1993,
109:
200
4c
Kusama T.
Wang T.-L.
Guggino WB.
Cutting GR.
Uhl GR.
Eur.
J. Pharmacol.
1993,
245:
83
5
Allan RD.
Johnston GAR.
Med. Res.
Rev.
1983,
3:
91
6a
Kennewell PD.
Matharu SS.
Tazlor JB.
West-wood R.
Sammes PG.
J.
Chem. Soc., Perkin Trans. 1
1982,
2563
6b
Paulini K.
Reissig H.-U.
Liebigs Ann. Chem.
1991,
455
6c
Morikawa T.
Sasaki H.
Hanai R.
Shibuya A.
Taguchi T.
J. Org.
Chem.
1994,
59:
97
6d
Galeazzi R.
Mobili G.
Orena M.
Tetrahedron: Asymmetry
1997,
8:
133
6e
Duke RK.
Allan RD.
Chebib M.
Greenwood JR.
Johnston GAR.
Tetrahedron: Asymmetry
1998,
9:
2533
6f
Forti L.
Ghelfi F.
Levizzani S.
Pagnoni UM.
Tetrahedron Lett.
1999,
40:
3233
6g
Bonnaud B.
Cousse H.
Mouzin G.
Briley M.
Stenger A.
Fauran F.
Couzinier J.-P.
J.
Med. Chem.
1987,
30:
318
6h
Galeazzi R.
Mobili G.
Orena M.
Tetrahedron
1999,
8:
261
7 Purchased from Fluka Cat. No. 46064;
solid support: methacrylamide/allyl glycidylether/methylene-bis-acrylamide;
loading: ˜500 U/g.
8 Enantiomeric ratio of 2 using
non-immobilized pig liver esterase: 100% ee.
[1a]
9
Born M.
Tamm C.
Synthesis
1991,
435
10 Purchased from Aldrich Cat. No.
21,644-5
11 Purchased from Fluka Cat. No. 81393;
solid support: poly(4-vinylpyridine)/25% DVB.
12 Purchased from Aldrich Cat. No. 36,834-2;
solid support: styrene/DVB; loading: 3.8 mmol/g.
13 Purchased from Fluka Cat. No. 57895;
solid support: styrene/>20% DVB; loading:
2.9 mmol/g.
14 Purchased from Fluka Cat. No. 93093;
solid support: styrene/2% DVB; loading: 3 mmol/g.
15 Purchased from Novabiochem Cat. No.
01-64-0178; solid support: styrene/1% DVB; loading
2.0-3.5 mmol/g.
16 Lit. value 8: [α]D
25 = -38.1
(c 1, 1 N HCl).
[6d]
17 Enantiomeric ratios of 10a-d using non-immobilized pig liver esterase: 10a: 100% ee, 10b:
90% ee, 10b: 9% ee, 10c: 78% ee.
[1a]
18 For the observed inconsistencies compare
reported optical rotation in references 1a and 1c. We wish to report
the following rotation 10a: [α]D
25 = -17.4
(c 0.8, CHCl3). Crystallographic
data of the amide formed from 12a and
(+)-(R)-α-methylbenzylamine have been deposited with the Cambridge
Crystallographic Data Centre as supplementary publication No. CCDC-189257.
Copies of the data can be obtained free of charge on application
to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(1223)336033; deposit@ccdc.cam.ac.uk).
19 For compound 10b we
measured [α]D
25 = -3.6
(c 0.95, CHCl3), which is
the opposite of the rotations published in references 1a,c.
20 According to the 13C
NMR spectrum the ratio of the diastereomers is 1:1.7.
21 Purchased from Novabiochem Cat. No.
01-64-0177; solid support: styrene/2% DVB; loading:
2.0-3.0 mmol/g.
22 Lit. values: 13a·HCl: [α]D
25 = -38.1
(c 1, 1 N HCl);
[6d]
13b·HCl: [α]D
25 = 24.1
(c 0.4, MeOH);
[6h]
analytical
data for 13d: 1H NMR
(400 MHz, D2O): δ = 1.25-1.71
(m, 8 H), 2.08-2.19 (m, 1 H), 2.43-2.50 (m, 1
H), 2.97 (dd, J = 12.8, 5.9
Hz, 1 H), 3.05 (dd, J = 12.8,
7.7 Hz, 1 H); 13C NMR (100 MHz, D2O): δ = 21.9,
24.5, 26.5, 27.3, 35.6, 40.6, 47.6, 183.6; 13d·HCl: [α]D
25 = 3.3
(c 1.1, MeOH).
23 Purchased from Novabiochem Cat. No.
01-64-0170; solid support: styrene/1% DVB; loading:
2.2 mmol/g.
24 Lit. value 15: [α]D
25 = 49.2
(c 1, CHCl3).
[6h]
25
Soai K.
Yokoyama S.
Mochida K.
Synthesis
1987,
647