1
44
Short Papers
SYNTHESIS
1
H NMR: d = 1.33 (d, 1 H, J = 9.3 Hz), 1.43 (d, 1 H, J = 9.3 Hz), 2.46
d, 1 H, J = 5.4 Hz), 2.78 (br s, 1 H), 2.83 (m, 1 H), 3.02 (br s, 1 H),
.28 (dd, 1 H, J = 5.6, 3.2 Hz), 6.29 (dd, 1 H, J = 5.6, 3.2 Hz), 7.34
(f) Magnus, P.; Carter, P.; Elliott, J.; Lewis, R.; Harling, J.; Pitter-
na, T.; Bauta, W. E.; Fortt, S. J. Am. Chem, Soc. 1992, 114, 2544.
(g) Magnus, P.; Lewis, R.; Bennett, F. J. Am. Chem. Soc. 1992,
114, 2560.
(
6
(m, 3 H), 7.68 (m, 3 H).
(
h) Jeong, N.; Lee, B. Y.; Lee, S. M.; Chung, Y. K.; Lee, S.-G.
Tetrahedron Lett. 1993, 34, 4023
(4-methylphenyl)sulfonyl]cyclopenta[c]pyrrol-5(1H)-one (Entry (3) (a) Smit, W. A.; Simonyan, S. O.; Tarasov, G. S.; Mikaelian, G.
Intramolecular Pauson–Khand Reaction: 2,3,3a,4-Tetrahydro-2-
[
2
, Table 2); Typical Procedure:
S.; Gybin, A. S.; Ibaragimov, I. I.; Caple, R.; Froen, O.; Kraeger,
A. Synthesis 1989, 472.
To an autoclave was added Co (CO) (29 mg, 0.05 mmol), tosylated
4
12
allyl propargyl amine (1.27 g, 5 mmol), and CH Cl (15 mL). The au-
(b) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron
Lett. 1990, 31, 5289.
2
2
toclave was flushed with N , charged with 10 atm of CO, and then
2
heated at 150°C for 23 h. After cooling to r.t., the solvent was evap-
(c) Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-E.
Synlett 1991, 204.
(d) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P.
L. Organometallics 1993, 12, 220.
orated and the crude product was flash chromatographed on a silica
4
gel column eluting with hexane/Et O; mp 142–145 °C (dec.) (Lit. mp
2
1
45–148 °C); yield: (87%).
1
(4) Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118,
H NMR: d = 2.06 (dd, 1 H, J = 5.4, 3.4 Hz), 2.44 (s, 3 H), 2.54–2.67
m, 2 H), 3.13–3.18 (m, 1 H), 4.03 (t, 2 H, J = 8.5 Hz), 4.34 (d, 1 H,
2
285.
(
(
5) For examples of the use of a catalytic amount of Co (CO) , see:
J = 16.6 Hz), 5.99 (s, 1 H), 7.35 (d, 2 H, J = 8.1 Hz), 7.74 (d, 2 H, J =
.3 Hz).
2
8
(
a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Fore-
man, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977.
b) Billington, D. C. Tetrahedron Lett. 1983, 24, 2905.
8
(
This work at the Center for Molecular Catalysis at Seoul National
University was supported by a grantfrom the Ministry ofEducation
(c) Magnus, P.; Principle, L. M.; SIater, M. J. J. Org. Chem. 1987,
52, 1483.
(d) Billington, D. C.; Kerr, W. J.; Pauson, P. L.; Farnochi, C. F.
J. Organomet. Chem. 1988, 356, 213.
(BSRI 97-3415) and the KOSEF
(
e) MacWhorter, S. E.; Sampath, V.; Olmstead, M. M.; Schore,
(1) (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J.
N. E. J. Org. Chem. 1988, 53, 203.
Chem. Soc., Chem. Commun. 1971, 36.
(f) Rautenstrauch, V.; Megard, P.; Conesa, J.; Kuster, W. Angew.
Chem., Int. Ed. Engl. 1990, 29, 1413.
(b) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J.
Chem. Soc., Perkin Trans. 1 1973, 977.
2) (a) Magnus, P.; Exon, C.; Albaugh-Robertson, P. Tetrahedron
(g) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem.
Soc. 1994, 116, 3159.
(
1
(
5
985, 41, 5861.
b) Magnus, P.; Principle, L. M.; Slater, M. J. Org. Chem. 1987,
2, 1483.
(h) For an example of the use of a catalytic amount of Co(acac)2
with/without NaBH , see: Lee, N. Y.; Chung, Y. K. Tetrahedron
4
Lett. 1996, 37, 3145.
(
5
(
c) Schore, N. E.; Rowley, E. G. J. Am. Chem. Soc. 1988, 110, (6) Guthrie, D. J. S.; Khand, I. U.; Knox, G. R.; Kollmeier, J.; Pau-
224.
son, P. L.; Watts, W. E. J. Organomet. Chem. 1975, 90, 93.
d) Rowley, E. G.; Schore, N. E. J. Organomet. Chem. 1991, 413, (7) (a) Bor, G.; Dietler, U. K.; Pino, P.; Poë, A. J. Organomet. Chem.
C5.
e) Magnus, P.; Fortt, S. M. J. Chem. Soc., Chem. Commun. 1991,
44.
1978, 154, 301.
(
5
(b) Bor, G.; Dietler, U. K. J. Organomet. Chem. 1980, 191, 295.
(8) Lee, N. Y. M. S. D. Thesis, Seoul National University, 1996.