-
1
-
-
52449100159
-
-
For a review discussing our strategy of using natural product structures to drive the development of enantioselective catalysis, see
-
For a review discussing our strategy of using natural product structures to drive the development of enantioselective catalysis, see: J.T. Mohr, M.R. Krout, and B.M. Stoltz Nature 455 2008 323 332
-
(2008)
Nature
, vol.455
, pp. 323-332
-
-
Mohr, J.T.1
Krout, M.R.2
Stoltz, B.M.3
-
2
-
-
9344253873
-
-
Ketone alkylation
-
For examples of asymmetric palladium-catalyzed reactions of cyclic ketone enolates, see: Ketone alkylation: D.C. Behenna, and B.M. Stoltz J. Am. Chem. Soc. 126 2004 15044 15045
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 15044-15045
-
-
Behenna, D.C.1
Stoltz, B.M.2
-
3
-
-
27544451620
-
-
J.T. Mohr, D.C. Behenna, A.M. Harned, and B.M. Stoltz Angew. Chem., Int. Ed. 44 2005 6924 6927
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 6924-6927
-
-
Mohr, J.T.1
Behenna, D.C.2
Harned, A.M.3
Stoltz, B.M.4
-
4
-
-
82255189929
-
-
doi:10.1002/chem.201003383 in press
-
Behenna, D. C.; Mohr, J. T.; Sherden, N. H.; Marinescu, S. C.; Harned, A. M.; Tani, K.; Seto, M.; Ma, S.; Novák, Z.; Krout, M. R.; McFadden, R. M.; Roizen, J. L.; Enquist, J. A.; White, D. E.; Levine, S. R.; Petrova, K. V.; Iwashita, A.; Virgil, S. C.; Stoltz, B. M. Chem. Eur. J., in press, doi:10.1002/chem.201003383
-
Chem. Eur. J.
-
-
Behenna, D.C.1
Mohr, J.T.2
Sherden, N.H.3
Marinescu, S.C.4
Harned, A.M.5
Tani, K.6
Seto, M.7
Ma, S.8
Novák, Z.9
Krout, M.R.10
McFadden, R.M.11
Roizen, J.L.12
Enquist, J.A.13
White, D.E.14
Levine, S.R.15
Petrova, K.V.16
Iwashita, A.17
Virgil, S.C.18
Stoltz, B.M.19
-
8
-
-
52449089307
-
-
For examples of the asymmetric palladium-catalyzed alkylation of heterocyclic ketone enolates, see
-
For examples of the asymmetric palladium-catalyzed alkylation of heterocyclic ketone enolates, see: M. Seto, J.L. Roizen, and B.M. Stoltz Angew. Chem., Int. Ed. 47 2008 6873 6876
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 6873-6876
-
-
Seto, M.1
Roizen, J.L.2
Stoltz, B.M.3
-
9
-
-
34848926246
-
-
For studies on the computational and experimental studies on the mechanism of palladium-catalyzed asymmetric alkylation using the PHOX ligand scaffold, see: J.A. Keith, D.C. Behenna, J.T. Mohr, S. Ma, S.C. Marinescu, J. Oxgaard, B.M. Stoltz, and W.A. Goddard J. Am. Chem. Soc. 129 2007 11876 11877
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 11876-11877
-
-
Keith, J.A.1
Behenna, D.C.2
Mohr, J.T.3
Ma, S.4
Marinescu, S.C.5
Oxgaard, J.6
Stoltz, B.M.7
Goddard, W.A.8
-
10
-
-
69549106158
-
-
N.H. Sherden, D.C. Behenna, S.C. Virgil, and B.M. Stoltz Angew. Chem., Int. Ed. 48 2009 6840 6843
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 6840-6843
-
-
Sherden, N.H.1
Behenna, D.C.2
Virgil, S.C.3
Stoltz, B.M.4
-
11
-
-
33745417849
-
-
For examples of the asymmetric alkylation of cyclic ketones and vinylogous esters or thioesters in the context of natural product synthesis, see: R.M. McFadden, and B.M. Stoltz J. Am. Chem. Soc. 128 2006 7738 7739
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 7738-7739
-
-
McFadden, R.M.1
Stoltz, B.M.2
-
15
-
-
77954243412
-
-
D.E. White, I.C. Stewart, B.A. Seashore-Ludlow, R.H. Grubbs, and B.M. Stoltz Tetrahedron 66 2010 4668 4686
-
(2010)
Tetrahedron
, vol.66
, pp. 4668-4686
-
-
White, D.E.1
Stewart, I.C.2
Seashore-Ludlow, B.A.3
Grubbs, R.H.4
Stoltz, B.M.5
-
16
-
-
79960284940
-
-
J.J. Day, R.M. McFadden, S.C. Virgil, H. Kolding, J.L. Alleva, and B.M. Stoltz Angew. Chem., Int. Ed. 50 2011 6814 6818
-
(2011)
Angew. Chem., Int. Ed.
, vol.50
, pp. 6814-6818
-
-
Day, J.J.1
McFadden, R.M.2
Virgil, S.C.3
Kolding, H.4
Alleva, J.L.5
Stoltz, B.M.6
-
17
-
-
5344279230
-
-
doi:10.1039/C1OB06189E For our initial communication on the addition of organometallic reagents to chiral vinylogous esters to form γ-quaternary cycloheptenones, see in press
-
For our initial communication on the addition of organometallic reagents to chiral vinylogous esters to form γ-quaternary cycloheptenones, see: Bennett, N. B.; Hong, A. Y.; Harned, A. M.; Stoltz, B. M. Org. Biomol. Chem., in press, doi:10.1039/C1OB06189E.
-
Org. Biomol. Chem.
-
-
Bennett, N.B.1
Hong, A.Y.2
Harned, A.M.3
Stoltz, B.M.4
-
18
-
-
79952498831
-
-
For our initial communication on the palladium catalyzed asymmetric alkylation and ring contraction studies in the synthesis of γ-quaternary acylcyclopentenes, see
-
For our initial communication on the palladium catalyzed asymmetric alkylation and ring contraction studies in the synthesis of γ-quaternary acylcyclopentenes, see: A.Y. Hong, M.R. Krout, T. Jensen, N.B. Bennett, A.M. Harned, and B.M. Stoltz Angew. Chem., Int. Ed. 50 2011 2756 2760
-
(2011)
Angew. Chem., Int. Ed.
, vol.50
, pp. 2756-2760
-
-
Hong, A.Y.1
Krout, M.R.2
Jensen, T.3
Bennett, N.B.4
Harned, A.M.5
Stoltz, B.M.6
-
19
-
-
1842637850
-
-
Concurrent with our efforts, palladium-catalyzed asymmetric allylic alkylations to form enantioenriched α-quaternary cyclic ketones and vinylogous esters/thioesters were reported by Trost. See: B.M. Trost, C. Pissot-Soldermann, I. Chen, and G.M. Schroeder J. Am. Chem. Soc. 126 2004 4480 4481
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 4480-4481
-
-
Trost, B.M.1
Pissot-Soldermann, C.2
Chen, I.3
Schroeder, G.M.4
-
24
-
-
0032358043
-
-
J.A. Ragan, T.W. Makowski, D.J. am Ende, P.J. Clifford, G.R. Young, A.K. Conrad, and S.A. Eisenbeis Org. Process Res. Dev. 2 1998 379 381
-
(1998)
Org. Process Res. Dev.
, vol.2
, pp. 379-381
-
-
Ragan, J.A.1
Makowski, T.W.2
Am Ende, D.J.3
Clifford, P.J.4
Young, G.R.5
Conrad, A.K.6
Eisenbeis, S.A.7
-
25
-
-
0035600912
-
-
J.A. Ragan, J.A. Murry, M.J. Castaldi, A.K. Conrad, B.P. Jones, B. Li, T.W. Makowski, R. McDermott, B.J. Sitter, T.D. White, and G.R. Young Org. Process Res. Dev. 5 2001 498 507
-
(2001)
Org. Process Res. Dev.
, vol.5
, pp. 498-507
-
-
Ragan, J.A.1
Murry, J.A.2
Castaldi, M.J.3
Conrad, A.K.4
Jones, B.P.5
Li, B.6
Makowski, T.W.7
McDermott, R.8
Sitter, B.J.9
White, T.D.10
Young, G.R.11
-
29
-
-
0002934419
-
-
T. Ukai, H. Kawazura, Y. Ishii, J.J. Bonnet, and J.A. Ibers J. Organomet. Chem. 65 1974 253 266
-
(1974)
J. Organomet. Chem.
, vol.65
, pp. 253-266
-
-
Ukai, T.1
Kawazura, H.2
Ishii, Y.3
Bonnet, J.J.4
Ibers, J.A.5
-
31
-
-
77956647486
-
-
3-t-Bu-PHOX), see: N.T. McDougal, J. Streuff, H. Mukherjee, S.C. Virgil, and B.M. Stoltz Tetrahedron Lett. 51 2010 5550 5554
-
(2010)
Tetrahedron Lett.
, vol.51
, pp. 5550-5554
-
-
McDougal, N.T.1
Streuff, J.2
Mukherjee, H.3
Virgil, S.C.4
Stoltz, B.M.5
-
33
-
-
79952513591
-
-
1H NMR spectra of 1,3-cyclohexadione (exclusively ketoenol form) and 1,3-cycloheptadione (exclusively diketo form). See Ref. 10c.: For selected examples of the two-carbon ring contraction of seven-membered carbocycles, see: J.J. Frankel, S. Julia, and C. Richard-Neuville Bull. Soc. Chim. Fr. 1968 4870 4875
-
(1968)
Bull. Soc. Chim. Fr.
, pp. 4870-4875
-
-
Frankel, J.J.1
Julia, S.2
Richard-Neuville, C.3
-
35
-
-
1542349357
-
-
While a recent report shows a single example of a similar β-hydroxyketone, we believe the unusual reactivity and synthetic potential of these compounds has not been fully explored
-
While a recent report shows a single example of a similar β-hydroxyketone, we believe the unusual reactivity and synthetic potential of these compounds has not been fully explored: H. Rinderhagen, and J. Mattay Chem. - Eur. J. 10 2004 851 874
-
(2004)
Chem. - Eur. J.
, vol.10
, pp. 851-874
-
-
Rinderhagen, H.1
Mattay, J.2
-
36
-
-
77955659950
-
-
For an example of a photochemical two-carbon ring contraction of a macrocycle, see
-
For an example of a photochemical two-carbon ring contraction of a macrocycle, see: Z. Yang, Y. Li, and G. Pattenden Tetrahedron 66 2010 6546 6549
-
(2010)
Tetrahedron
, vol.66
, pp. 6546-6549
-
-
Yang, Z.1
Li, Y.2
Pattenden, G.3
-
44
-
-
0346970844
-
-
For a discussion of the properties of fluorinated alcohols and their use, see
-
For a discussion of the properties of fluorinated alcohols and their use, see: J.-P. Begue, D. Bonnet-Delphon, and B. Crousse Synlett 2004 18 29
-
(2004)
Synlett
, pp. 18-29
-
-
Begue, J.-P.1
Bonnet-Delphon, D.2
Crousse, B.3
-
45
-
-
0344887064
-
-
A lithium alkoxide species is presumably generated in situ based on the following pKa values: (H2O=15.7, TFE=12.5, HFIP=9.3 [water]; H2O=31.2, TFE=23.5, HFIP=18.2 [DMSO])
-
A lithium alkoxide species is presumably generated in situ based on the following pKa values: (H2O=15.7, TFE=12.5, HFIP=9.3 [water]; H2O=31.2, TFE=23.5, HFIP=18.2 [DMSO]); F.G. Bordwell Acc. Chem. Res. 21 1988 456 463
-
(1988)
Acc. Chem. Res.
, vol.21
, pp. 456-463
-
-
Bordwell, F.G.1
-
46
-
-
25444458327
-
-
Fluorinated lithium alkoxides were recently used to promote Horner-Wadsworth-Emmons olefinations of sensitive substrates, demonstrating their mild reactivity
-
Fluorinated lithium alkoxides were recently used to promote Horner-Wadsworth-Emmons olefinations of sensitive substrates, demonstrating their mild reactivity: L.K. Blasdel, and A.G. Myers Org. Lett. 7 2005 4281 4283
-
(2005)
Org. Lett.
, vol.7
, pp. 4281-4283
-
-
Blasdel, L.K.1
Myers, A.G.2
-
48
-
-
0026725542
-
-
The addition of cerium chloride to reactions with organolithium or Grignard reagents has been shown to increase reactivity and reduce side reactions with vinylogous ester systems, see
-
Analytically pure samples of dione 17 can be obtained from vinylogous ester 7a by treatment with acid. See Supplementary data for details.: The addition of cerium chloride to reactions with organolithium or Grignard reagents has been shown to increase reactivity and reduce side reactions with vinylogous ester systems, see: M.T. Crimmins, and D. Dedopoulou Synth. Commun. 22 1992 1953 1958
-
(1992)
Synth. Commun.
, vol.22
, pp. 1953-1958
-
-
Crimmins, M.T.1
Dedopoulou, D.2
-
50
-
-
84888899999
-
-
W.A. Herrmann, K.O. Brossmer, C.-P. Reisinger, T. Priermeier, M. Beller, and H. Fischer Angew. Chem., Int. Ed. Engl. 34 1995 1845 1848
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 1845-1848
-
-
Herrmann, W.A.1
Brossmer, K.O.2
Reisinger, C.-P.3
Priermeier, T.4
Beller, M.5
Fischer, H.6
-
52
-
-
0000795340
-
-
Y.K. Chung, B.Y. Lee, N. Jeong, M. Hudecek, and P.L. Pauson Organometallics 12 1993 220 223
-
(1993)
Organometallics
, vol.12
, pp. 220-223
-
-
Chung, Y.K.1
Lee, B.Y.2
Jeong, N.3
Hudecek, M.4
Pauson, P.L.5
|