Chemistry Reference
In-Depth Information
[13] For the use of chiral ligands attached to metals other than cobalt, see: (a) F. A. Hicks
and S. L. Buchwald, Highly enantioselective catalytic Pauson-Khand type formation
of bicyclic cyclopentenones,
J. Am. Chem. Soc.
118
, 11688 (1996); (b) S. J. Sturla
and S. L. Buchwald, Catalytic asymmetric cyclocarbonylation of nitrogen-containing
enynes,
J. Org. Chem.
64
, 5547 (1999); (c) F. A. Hicks and S. L. Buchwald, An
intramolecular titanium-catalyzed asymmetric Pauson-Khand type reaction,
J. Am.
Chem. Soc.
121
, 7026 (1999); (d) N. Jeong, B. K. Sung, and Y. K. Choi, Rhodium(I)-
catalyzed asymmetric intramolecular Pauson-Khand-type reaction,
J. Am. Chem. Soc.
122
, 6771 (2000); (e) T. Shibata and K. Takagi, Iridium-chiral diphosphine complex
catalyzed highly enantioselective Pauson-Khand-type reaction,
J. Am. Chem. Soc.
122
, 9852 (2000).
[14] A. Moyano, F. Charbonnier, and A. E. Greene, A simple preparation of chiral
acetylenic ethers,
J. Org. Chem.
52
, 2919 (1987).
[15] For another approach to alkoxyacetylenes, see: M. A. Pericas, F. Serratosa, and E.
Valentı, An efficient synthesis of
tert
-alkoxyethynes,
Tetrahedron
43
, 2311 (1987).
[16] M. Poch, E. Valentı, A. Moyano, M. A. Pericas, J. Castro, A. DeNicola, and A. E.
Greene, Asymmetric induction studies in the intramolecular Pauson-Khand cyclization
of 1-alkoxy-1-hepten-6-ynes,
Tetrahedron Lett.
31
, 7505 (1990).
[17] J. Castro, A. Moyano, M. A. Pericas, and A. Riera, A qualitative molecular me-
chanics approach to the stereoselectivity in intramolecular Pauson-Khand reactions,
Tetrahedron
51
, 6541 (1995).
[18] X. Verdaguer, A. Moyano, M. A. Pericas, A. Riera, A. E. Greene, J. F. Piniella,
and A. Alvarez-Larena, Camphor-derived alcohols as chiral auxiliaries for asymmet-
ric Pauson-Khand bicyclizations. Enantioselective synthesis of
-methoxyenones,
J.
Organomet. Chem.
433
, 305 (1992).
[19] First examples: (a) M. J. Knudsen and N. E. Schore, Synthesis of the angularly fused
triquinane skeleton via intramolecular organometallic cyclization,
J. Org. Chem.
49
,
5025 (1984); (b) E. Carceller, V. Centellas, A. Moyano, M. A. Pericas, and F. Serratosa,
Direct entry to the all-cis tricyclo[5.2.1.0
4,10
]decane (perhydrotriquinacene) skeleton
by a cobalt mediated intramolecular cyclization,
Tetrahedron Lett.
26
, 2475 (1985);
(c) W. A. Smit, A. S. Gybin, A.S. Shashkov, Y. T. Strychkov, L. G. Kyz'mina, G. S.
Mikaelian, R. Caple, and E. D. Swanson, New route to the synthesis of polycyclic
compounds based on a stepwise Ad
E
-reaction of dicobalt hexacarbonyl complexes of
conjugated enynes with a subsequent intramolecular Khand-Pauson reaction,
Tetrahe-
dron Lett.
27
, 1241 (1986); (d) E. Carceller, M. L. Garcıa, A. Moyano, M. A. Pericas,
and F. Serratosa, Synthesis of triquinacene derivatives. A new approach towards the
synthesis of dodecahedrane,
Tetrahedron
42
, 1831 (1986); (e) S. L. Schreiber, T.
Sammakia, and W. E. Crowe, Lewis acid mediated version of the Nicholas reaction:
synthesis of
syn
-alkylated products and cobalt-complexed cycloalkynes,
J. Am. Chem.
Soc.
108
, 3128 (1986); (f) N. E. Schore and M. J. Knudsen, Two approaches to angu-
larly fused triquinanes via intramolecular Pauson-Khand reaction,
J. Org. Chem.
52
,
569 (1987); (g) C. Almansa, A. Moyano, and F. Serratosa, Synthesis and chiroptical
properties of
C
3
-perhydrotriquinacene derivatives,
Tetrahedron
44
, 2657 (1988); (h)
N. E. Schore and E. G. Rowley, Diastereofacial selectivity in intramolecular Pauson-
Khand cycloadditions: highly stereoselective synthesis of pentalenene,
J. Am. Chem.
Soc.
110
, 5224 (1988).