-
1
-
-
44949088226
-
-
Organometallic enantiomeric scaffolds: (1) the metal/ligand auxiliary attached to the unsaturated ligand influences novel reactions, controls non-traditional selectivities, and provides a dominant regio- and stereocontrol element on the scaffold that allows the predictable introduction of new stereocenters at multiple sites around the unsaturated ligand, (2) a single metal/ligand auxiliary controls the introduction of multiple stereocenters over multiple steps, and (3) the organometallic nature of the scaffolding enables the use of stereodivergent tactics for the introduction of ring substituents.
-
Organometallic enantiomeric scaffolds: (1) the metal/ligand auxiliary attached to the unsaturated ligand influences novel reactions, controls non-traditional selectivities, and provides a dominant regio- and stereocontrol element on the scaffold that allows the predictable introduction of new stereocenters at multiple sites around the unsaturated ligand, (2) a single metal/ligand auxiliary controls the introduction of multiple stereocenters over multiple steps, and (3) the organometallic nature of the scaffolding enables the use of stereodivergent tactics for the introduction of ring substituents.
-
-
-
-
2
-
-
38849138620
-
-
Coombs, T. C.; Lee IV, M. D.; Wong, H.; Armstrong, M.; Cheng, B.; Chen, W.; Moretto, A. F.; Liebeskind, L. S. J. Org. Chem. 2008, 73, 882-888.
-
(2008)
J. Org. Chem
, vol.73
, pp. 882-888
-
-
Coombs, T.C.1
Lee2
IV, M.D.3
Wong, H.4
Armstrong, M.5
Cheng, B.6
Chen, W.7
Moretto, A.F.8
Liebeskind, L.S.9
-
4
-
-
0035915320
-
-
Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477-12487.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 12477-12487
-
-
Shu, C.1
Alcudia, A.2
Yin, J.3
Liebeskind, L.S.4
-
5
-
-
0034715462
-
-
Yin, J.; Llorente, I.; Villanueva, L. A.; Liebeskind, L. S. J. Am. Chem. Soc. 2000, 122, 10458-10459.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 10458-10459
-
-
Yin, J.1
Llorente, I.2
Villanueva, L.A.3
Liebeskind, L.S.4
-
10
-
-
33847000571
-
-
Arrayás, R. G.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 1816-1825.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 1816-1825
-
-
Arrayás, R.G.1
Yin, J.2
Liebeskind, L.S.3
-
16
-
-
33745698664
-
-
Pollini, G. P.; Benetti, S.; Risi, C. D.; Zanirato, V. Chem. Rev. 2006, 106, 2434-2454.
-
(2006)
Chem. Rev
, vol.106
, pp. 2434-2454
-
-
Pollini, G.P.1
Benetti, S.2
Risi, C.D.3
Zanirato, V.4
-
18
-
-
0037008931
-
-
Nair, V.; Treesa, P. M.; Rath, N. P.; Kunwar, A. C.; KiranKumar, K. S.; RaviSankar, A.; Vairamani, M.; Prabhakar, S. Tetrahedron Lett. 2002, 58, 7221-7231.
-
(2002)
Tetrahedron Lett
, vol.58
, pp. 7221-7231
-
-
Nair, V.1
Treesa, P.M.2
Rath, N.P.3
Kunwar, A.C.4
KiranKumar, K.S.5
RaviSankar, A.6
Vairamani, M.7
Prabhakar, S.8
-
19
-
-
33748482185
-
-
Singh, S. B.; Jayasuriya, H.; Ondeyka, J. G.; Herath, K. B.; Zhang, C.; Zink, D. L.; Tsou, N. N.; Ball, R. G.; Basilio, A.; Genilloud, O.; Diez, M. T.; Vicente, F.; Pelaez, F.; Young, K.; Wang, J. J. Am. Chem. Soc. 2006, 128, 11916-11920.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 11916-11920
-
-
Singh, S.B.1
Jayasuriya, H.2
Ondeyka, J.G.3
Herath, K.B.4
Zhang, C.5
Zink, D.L.6
Tsou, N.N.7
Ball, R.G.8
Basilio, A.9
Genilloud, O.10
Diez, M.T.11
Vicente, F.12
Pelaez, F.13
Young, K.14
Wang, J.15
-
20
-
-
14944341806
-
-
Han, L.; Huang, X.; Sattler, I.; Moellmann, U.; Fu, H.; Lin, W.; Grabley, S. Planta Med. 2005, 71, 160-164.
-
(2005)
Planta Med
, vol.71
, pp. 160-164
-
-
Han, L.1
Huang, X.2
Sattler, I.3
Moellmann, U.4
Fu, H.5
Lin, W.6
Grabley, S.7
-
21
-
-
2542533185
-
-
Shen, Y.-H.; Li, S.-H.; Li, R.-T.; Han, Q.-B.; Zhao, Q.-S.; Liang, L.; Sun, H.-D.; Lu, Y.; Cao, P.; Zheng, Q.-T. Org. Lett. 2004, 6, 1593-1595.
-
(2004)
Org. Lett
, vol.6
, pp. 1593-1595
-
-
Shen, Y.-H.1
Li, S.-H.2
Li, R.-T.3
Han, Q.-B.4
Zhao, Q.-S.5
Liang, L.6
Sun, H.-D.7
Lu, Y.8
Cao, P.9
Zheng, Q.-T.10
-
22
-
-
0004136903
-
-
Harmata, M, Ed, JAI Press: Stamford, CT
-
Wender, P. A.; Love, J. A. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; pp 1-45..
-
(1999)
Advances in Cycloaddition
, pp. 1-45
-
-
Wender, P.A.1
Love, J.A.2
-
23
-
-
0003075009
-
-
Metz, P, Ed, Springer-Verlag: Berlin
-
Chiu, P.; Lautens, M. In Topic in Current Chemistry; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 190; pp 1-85..
-
(1997)
Topic in Current Chemistry
, vol.190
, pp. 1-85
-
-
Chiu, P.1
Lautens, M.2
-
27
-
-
0038742052
-
-
Baldwin, J. E.; Mayweg, A. V. W.; Pritchard, G. J.; Adlington, R. M. Tetrahedron Lett. 2003, 44, 4543-4545.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 4543-4545
-
-
Baldwin, J.E.1
Mayweg, A.V.W.2
Pritchard, G.J.3
Adlington, R.M.4
-
28
-
-
0024827695
-
-
Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954-8957.
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 8954-8957
-
-
Wender, P.A.1
Lee, H.Y.2
Wilhelm, R.S.3
Williams, P.D.4
-
29
-
-
37049106933
-
-
Furneaux, R. H.; Mason, J. M.; Miller, I. J. J. Chem. Soc., Perkin Trans. 1 1984, 1923-1928.
-
(1984)
J. Chem. Soc., Perkin Trans. 1
, pp. 1923-1928
-
-
Furneaux, R.H.1
Mason, J.M.2
Miller, I.J.3
-
30
-
-
0035951941
-
-
Lee, H.-Y.; Sohn, J.-H.; Kim, H. Y. Tetrahedron Lett. 2001, 42, 1695-1698.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 1695-1698
-
-
Lee, H.-Y.1
Sohn, J.-H.2
Kim, H.Y.3
-
31
-
-
33846325856
-
-
Roethle, P. A.; Hernandez, P. T.; Trauner, D. Org. Lett. 2006, 8, 5901-5904.
-
(2006)
Org. Lett
, vol.8
, pp. 5901-5904
-
-
Roethle, P.A.1
Hernandez, P.T.2
Trauner, D.3
-
32
-
-
7044240215
-
-
Krishna, U. M.; Srikanth, G. S. C.; Trivedi, G. K.; Deodhar, K. D. Synlett 2003, 2383-2385.
-
(2003)
Synlett
, pp. 2383-2385
-
-
Krishna, U.M.1
Srikanth, G.S.C.2
Trivedi, G.K.3
Deodhar, K.D.4
-
33
-
-
0000869351
-
-
Williams, D. R.; Benbow, J. W.; McNutt, J. G.; Allen, E. E. J. Org. Chem. 1995, 60, 833-843.
-
(1995)
J. Org. Chem
, vol.60
, pp. 833-843
-
-
Williams, D.R.1
Benbow, J.W.2
McNutt, J.G.3
Allen, E.E.4
-
34
-
-
0030884126
-
-
Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
-
(1997)
J. Am. Chem. Soc
, vol.119
, pp. 7897-7898
-
-
Wender, P.A.1
Rice, K.D.2
Schnute, M.E.3
-
35
-
-
2342586551
-
-
Krishna, U. M.; Deodhar, K. D.; Trivedi, G. K. Tetrahedron 2004, 60, 4829-4836.
-
(2004)
Tetrahedron
, vol.60
, pp. 4829-4836
-
-
Krishna, U.M.1
Deodhar, K.D.2
Trivedi, G.K.3
-
36
-
-
33845236874
-
-
Wender, P. A.; Bi, F. C.; Buschmann, N.; Gosselin, N.; Kan, C.; Kee, J.-M.; Ohmura, H. Org. Lett. 2006, 8, 5373-5376.
-
(2006)
Org. Lett
, vol.8
, pp. 5373-5376
-
-
Wender, P.A.1
Bi, F.C.2
Buschmann, N.3
Gosselin, N.4
Kan, C.5
Kee, J.-M.6
Ohmura, H.7
-
37
-
-
0034601161
-
-
Prakash, K. R. C.; Trzcinska, M.; Johnson, K. M.; Kozikowski, A. P. Bioorg. Med. Chem. Lett. 2000, 10, 1443-1446.
-
(2000)
Bioorg. Med. Chem. Lett
, vol.10
, pp. 1443-1446
-
-
Prakash, K.R.C.1
Trzcinska, M.2
Johnson, K.M.3
Kozikowski, A.P.4
-
39
-
-
0037047523
-
-
Alcudia, A.; Arrayás, R. G.; Liebeskind, L. S. J. Org. Chem. 2002, 67, 5773-5778.
-
(2002)
J. Org. Chem
, vol.67
, pp. 5773-5778
-
-
Alcudia, A.1
Arrayás, R.G.2
Liebeskind, L.S.3
-
40
-
-
0002710889
-
-
Chemical Equation Presented
-
Nakagawa, M.; Saegusa, J.; Tonozuka, M.; Obi, M.; Kiuchi, M.; Hino, T.; Ban, Y. Org. Synth. 1977, 56, 49-52 (Chemical Equation Presented)
-
(1977)
Org. Synth
, vol.56
, pp. 49-52
-
-
Nakagawa, M.1
Saegusa, J.2
Tonozuka, M.3
Obi, M.4
Kiuchi, M.5
Hino, T.6
Ban, Y.7
-
41
-
-
0000596906
-
-
Ward, Y. D.; Villanueva, L. A.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 897-898.
-
(1996)
J. Am. Chem. Soc
, vol.118
, pp. 897-898
-
-
Ward, Y.D.1
Villanueva, L.A.2
Allred, G.D.3
Liebeskind, L.S.4
-
43
-
-
33645349856
-
-
Areces, P.; Carrasco, E.; Mancha, A.; Plumet, J. Synthesis 2006, 946-948.
-
(2006)
Synthesis
, pp. 946-948
-
-
Areces, P.1
Carrasco, E.2
Mancha, A.3
Plumet, J.4
-
44
-
-
44949186157
-
-
Yadav, J. S.; Subba Reddy, B. V.; Suresh Reddy, C. Tetrahedron Lett. 2004, 45, 4585-4585.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 4585-4585
-
-
Yadav, J.S.1
Subba Reddy, B.V.2
Suresh Reddy, C.3
-
45
-
-
44949230894
-
-
The other antipode (R)-6 would be available starting from L-arabinose following the same synthetic sequence.
-
The other antipode (R)-6 would be available starting from L-arabinose following the same synthetic sequence.
-
-
-
-
46
-
-
0001691827
-
-
Nesmeyanov, A. N.; Krivykh, V. V.; Kaganovich, V. S.; Rybinskaya, M. I. J. Organomet. Chem. 1975, 102, 185-193.
-
(1975)
J. Organomet. Chem
, vol.102
, pp. 185-193
-
-
Nesmeyanov, A.N.1
Krivykh, V.V.2
Kaganovich, V.S.3
Rybinskaya, M.I.4
-
48
-
-
0035909647
-
-
Arrayás, R. G.; Alcudia, A.; Liebeskind, L. S. Org. Lett. 2001, 3, 3381-3383.
-
(2001)
Org. Lett
, vol.3
, pp. 3381-3383
-
-
Arrayás, R.G.1
Alcudia, A.2
Liebeskind, L.S.3
-
50
-
-
0036187765
-
-
Commercially available from Tokyo Kasei Kogyo Co., Ltd (TCI). For a reliable procedure, see: Matsuo, J.-i.; Iida, D.; Tatani, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 223-234.
-
Commercially available from Tokyo Kasei Kogyo Co., Ltd (TCI). For a reliable procedure, see: Matsuo, J.-i.; Iida, D.; Tatani, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 223-234.
-
-
-
-
51
-
-
44949237676
-
-
The absolute configuration of scaffolds (+)-4 and (-)-4 was determined through the synthesis of R-(-)-coniine starting from scaffold (Chemical Equation Presented)
-
The absolute configuration of scaffolds (+)-4 and (-)-4 was determined through the synthesis of R-(-)-coniine starting from scaffold (Chemical Equation Presented)
-
-
-
-
52
-
-
44949141192
-
-
This reagent was obtained from condensation of (S)-1-phenylbutanol with CDI in the presence of catalytic DMAP in dichloromethane. For more details, see the Supporting Information
-
This reagent was obtained from condensation of (S)-1-phenylbutanol with CDI in the presence of catalytic DMAP in dichloromethane. For more details, see the Supporting Information.
-
-
-
-
53
-
-
44949193494
-
-
Introduction of the chiral auxiliary directly onto compound 13 was problematic, especially at the purification stage. The sequence indicated in the text proved more flexible and allowed isolation of both racemic and chiral, nonracemic scaffolds.
-
Introduction of the chiral auxiliary directly onto compound 13 was problematic, especially at the purification stage. The sequence indicated in the text proved more flexible and allowed isolation of both racemic and chiral, nonracemic scaffolds.
-
-
-
-
54
-
-
33751386487
-
-
Boyd, V. A.; Drake, B. E.; Sulikowski, G. A. J. Org. Chem. 1993, 58, 3191-3193.
-
(1993)
J. Org. Chem
, vol.58
, pp. 3191-3193
-
-
Boyd, V.A.1
Drake, B.E.2
Sulikowski, G.A.3
-
55
-
-
33646057693
-
-
Li, H.; Procko, K.; Martin, S. F. Tetrahedron Lett. 2006, 47, 3485-3488.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 3485-3488
-
-
Li, H.1
Procko, K.2
Martin, S.F.3
-
56
-
-
44949224751
-
-
Addition of Grignard reagents at-40°C was followed by trapping of the hemiketal at - 78°C for 1 h. The reaction mixture was then allowed to warm over 2 h.
-
Addition of Grignard reagents at-40°C was followed by trapping of the hemiketal at - 78°C for 1 h. The reaction mixture was then allowed to warm over 2 h.
-
-
-
-
57
-
-
44949132756
-
-
1H MR spectra.
-
1H MR spectra.
-
-
-
-
58
-
-
19544372137
-
-
Garnett, J. L.; Long, M. A.; Vining, R. F. W.; Mole, T. Tetrahedron Lett. 1973, 4075-4078.
-
(1973)
Tetrahedron Lett
, pp. 4075-4078
-
-
Garnett, J.L.1
Long, M.A.2
Vining, R.F.W.3
Mole, T.4
-
59
-
-
0000991724
-
-
Magagnini, P. L.; Cesca, S.; Giusti, P.; Priola, P.; Di Maina, M. Makromol. Chem. 1977, 178, 2235-2248.
-
(1977)
Makromol. Chem
, vol.178
, pp. 2235-2248
-
-
Magagnini, P.L.1
Cesca, S.2
Giusti, P.3
Priola, P.4
Di Maina, M.5
-
60
-
-
44949196434
-
-
2,4-Di-tert-butyl-4-hydroxytoluene (BHT), the stabilizer used in commercially available ethyl vinyl ketone, could also generate a super Brønsted acid but is assumed to be too hindered to be effective.
-
2,4-Di-tert-butyl-4-hydroxytoluene (BHT), the stabilizer used in commercially available ethyl vinyl ketone, could also generate a "super Brønsted acid" but is assumed to be too hindered to be effective.
-
-
-
-
61
-
-
33144456572
-
-
Huscroft, I. T.; Carlson, E. J.; Chicchi, G. G.; Kurtz, M. M.; London, C.; Raubo, P.; Wheeldom, A.; Kulagowski, J. J. Bioorg. Med. Chem. Lett. 2006, 16, 2008-2012.
-
(2006)
Bioorg. Med. Chem. Lett
, vol.16
, pp. 2008-2012
-
-
Huscroft, I.T.1
Carlson, E.J.2
Chicchi, G.G.3
Kurtz, M.M.4
London, C.5
Raubo, P.6
Wheeldom, A.7
Kulagowski, J.J.8
-
62
-
-
30344450817
-
-
Thompson, C. G.; Carlson, E.; Chicchi, G. G.; Kulagowski, J. J.; Kurtz, M. M.; Swain, C. J.; Tsao, K.-L. C.; Wheeldom, A. Bioorg. Med. Chem. Lett. 2006, 16, 811-814.
-
(2006)
Bioorg. Med. Chem. Lett
, vol.16
, pp. 811-814
-
-
Thompson, C.G.1
Carlson, E.2
Chicchi, G.G.3
Kulagowski, J.J.4
Kurtz, M.M.5
Swain, C.J.6
Tsao, K.-L.C.7
Wheeldom, A.8
-
63
-
-
0042905751
-
-
López, F.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2000, 2, 1005-1007.
-
(2000)
Org. Lett
, vol.2
, pp. 1005-1007
-
-
López, F.1
Castedo, L.2
Mascareñas, J.L.3
|