-
2
-
-
0039841696
-
-
(a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335-422.
-
(1973)
Coord. Chem. Rev.
, vol.10
, pp. 335-422
-
-
Appleton, T.G.1
Clark, H.C.2
Manzer, L.E.3
-
3
-
-
4243434656
-
-
(b) Murray, S.; Hartley, F. Chem. Rev. 1981, 81, 365-414. The general trend for the trans influences of ligand donors is: PR3 > SR2 > C5H5N > R2NH ≫ OR2.
-
(1981)
Chem. Rev.
, vol.81
, pp. 365-414
-
-
Murray, S.1
Hartley, F.2
-
4
-
-
0033617173
-
-
For a preliminary account of this work see: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994-2995.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 2994-2995
-
-
Evans, D.A.1
Campos, K.R.2
Tedrow, J.S.3
Michael, F.E.4
Gagné, M.R.5
-
5
-
-
6844254916
-
-
and references therein
-
For a general review of the asymmetric transition metal-catalyzed allylic alkylation, see: Trost, B. M; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422 and references therein.
-
(1996)
Chem. Rev.
, vol.96
, pp. 395-422
-
-
Trost, B.M.1
Van Vranken, D.L.2
-
6
-
-
1542694981
-
-
(a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 7932-7934
-
-
Miyashita, A.1
Yasuda, A.2
Takaya, H.3
Toriumi, K.4
Ito, T.5
Souchi, T.6
Noyori, R.7
-
9
-
-
0028882906
-
-
(d) Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kuhnle, F. N. M.; Schweizer, W. B.; Weber, B. Helv. Chem. Acta 1995, 78, 1636-1650.
-
(1995)
Helv. Chem. Acta
, vol.78
, pp. 1636-1650
-
-
Seebach, D.1
Devaquet, E.2
Ernst, A.3
Hayakawa, M.4
Kuhnle, F.N.M.5
Schweizer, W.B.6
Weber, B.7
-
10
-
-
0000390005
-
-
and references therein
-
(a) Pfaltz, A. Acta Chim. Scand. 1996, 50, 189-194 and references therein.
-
(1996)
Acta Chim. Scand.
, vol.50
, pp. 189-194
-
-
Pfaltz, A.1
-
11
-
-
0032538768
-
-
(b) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
-
(1998)
Angew. Chem., Int. Ed. Engl.
, vol.37
, pp. 3047-3050
-
-
Kudis, S.1
Helmchen, G.2
-
12
-
-
0027196559
-
-
(C) Dawson, G. J.; Frost, G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 3149-3150.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 3149-3150
-
-
Dawson, G.J.1
Frost, G.2
Williams, J.M.J.3
-
14
-
-
0032513157
-
-
(b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 753-756
-
-
Anderson, J.C.1
James, D.S.2
Mathias, J.P.3
-
15
-
-
0028349296
-
-
(c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526.
-
(1994)
Tetrahedron Lett.
, vol.10
, pp. 1523-1526
-
-
Sprinz, J.1
Keifer, M.2
Helmchen, G.3
Regglein, M.4
Huttner, G.5
Walter, O.6
Zsolanai, L.7
-
16
-
-
0027997952
-
-
(d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 1895-1898
-
-
Allen, J.1
Bower, J.2
Williams, J.3
-
17
-
-
0001670942
-
-
(e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264.
-
(1998)
Organometallics
, vol.17
, pp. 3254-3264
-
-
Boog-Wick, K.1
Pregosin, P.2
Trabesinger, G.3
-
19
-
-
0028146009
-
-
(b) Gladiali, S.; Dore, A.; Fabbri, D. Tetrahedron: Asymmetry 1994, 5, 1143-1146.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 1143-1146
-
-
Gladiali, S.1
Dore, A.2
Fabbri, D.3
-
20
-
-
0031979280
-
-
(c) Hiraoka, M.; Nishikawa, A.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 704-706.
-
(1998)
Chem. Pharm. Bull.
, vol.46
, pp. 704-706
-
-
Hiraoka, M.1
Nishikawa, A.2
Morimoto, T.3
Achiwa, K.4
-
22
-
-
0000918702
-
-
(e) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
-
(1998)
Organometallics
, vol.17
, pp. 4976-4982
-
-
Hauptman, E.1
Shapiro, R.2
Marshall, W.3
-
23
-
-
0031979280
-
-
(f) Hiraoka, M.; Nishikawa, A.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 704-707.
-
(1998)
Chem. Pharm. Bull.
, vol.46
, pp. 704-707
-
-
Hiraoka, M.1
Nishikawa, A.2
Morimoto, T.3
Achiwa, K.4
-
24
-
-
0000748306
-
-
(g) Enders, D.; Peters, R.; Runsink, J.; Bats, J. W. Org. Lett. 1999, 1, 1863-1866.
-
(1999)
Org. Lett.
, vol.1
, pp. 1863-1866
-
-
Enders, D.1
Peters, R.2
Runsink, J.3
Bats, J.W.4
-
25
-
-
0002450988
-
-
(a) Abel, E.; Bhargava, S. K.; Orrell, K. G. Prog. Inorg. Chem. 1984, 32, 1-118.
-
(1984)
Prog. Inorg. Chem.
, vol.32
, pp. 1-118
-
-
Abel, E.1
Bhargava, S.K.2
Orrell, K.G.3
-
26
-
-
37049066854
-
-
(b) Abel, E.; Dormer, J.; Ellis, D.; Orrell, K. G.; Sik, V.; Hursthouse, M. B.; Mazid, M. A. J. Chem. Soc., Dalton Trans. 1992, 1073-1080.
-
(1992)
J. Chem. Soc., Dalton Trans.
, pp. 1073-1080
-
-
Abel, E.1
Dormer, J.2
Ellis, D.3
Orrell, K.G.4
Sik, V.5
Hursthouse, M.B.6
Mazid, M.A.7
-
27
-
-
3743127668
-
-
and references therein
-
Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein.
-
(1996)
Organometallics
, vol.15
, pp. 2419-2421
-
-
Albinati, A.1
Pregosin, P.2
Wick, K.3
-
28
-
-
0001266126
-
-
and references therein
-
Albinati, A.; Eckert, J.; Pregosin, P.; Ruegger, H.; Salzmann, R.; Stossel, C. Organometallics 1997, 16, 579-590 and references therein.
-
(1997)
Organometallics
, vol.16
, pp. 579-590
-
-
Albinati, A.1
Eckert, J.2
Pregosin, P.3
Ruegger, H.4
Salzmann, R.5
Stossel, C.6
-
29
-
-
0342983409
-
-
note
-
Enhanced enantioselectivities were observed with increased chelate size using chiral diphosphines, reflective of a greater penetration of the (P)-phenyl rings into the space occupied by the π-allyl moiety. Reference 5b.
-
-
-
-
30
-
-
33847800667
-
-
P-chiral diphosphines also have stereogenicity close to the metal center. For examples of the application of the P-chiral diphosphine DIPAMP in asymmetric catalysis see: (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauff, D. J. J. Am. Chem. Soc. 1975, 97, 2567-2568. (b) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 2567-2568
-
-
Knowles, W.S.1
Sabacky, M.J.2
Vineyard, B.D.3
Weinkauff, D.J.4
-
31
-
-
0000313407
-
-
P-chiral diphosphines also have stereogenicity close to the metal center. For examples of the application of the P-chiral diphosphine DIPAMP in asymmetric catalysis see: (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauff, D. J. J. Am. Chem. Soc. 1975, 97, 2567-2568. (b) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.
-
(1977)
J. Am. Chem. Soc.
, vol.99
, pp. 5946-5952
-
-
Vineyard, B.D.1
Knowles, W.S.2
Sabacky, M.J.3
Bachman, G.L.4
Weinkauff, D.J.5
-
32
-
-
0001266126
-
-
and references therein
-
It has been noted by Pregosin and co-workers that conformationally flexible mixed phosphorus/sulfur ligand chelates suffered from sulfur inversion at ambient temperature. Albinati, A.; Eckert, J.; Pregosin, P.; Ruegger, H.; Salzmann, R.; Stossel, C. Organometallics 1997, 16, 579-590 and references therein.
-
(1997)
Organometallics
, vol.16
, pp. 579-590
-
-
Albinati, A.1
Eckert, J.2
Pregosin, P.3
Ruegger, H.4
Salzmann, R.5
Stossel, C.6
-
33
-
-
0030830130
-
-
and references therein
-
Walford, C.; Jackson, R. F. W.; Rees, N. H.; Clegg, W.; Heath, S. J. Chem. Soc., Chem. Commun. 1997, 1855-1856 and references therein.
-
(1997)
J. Chem. Soc., Chem. Commun.
, pp. 1855-1856
-
-
Walford, C.1
Jackson, R.F.W.2
Rees, N.H.3
Clegg, W.4
Heath, S.5
-
34
-
-
0028214617
-
-
(a) Enders, D.; Schäfer, T.; Piva, O.; Zamponi, A. Tetrahedron 1994, 50, 3349-3362.
-
(1994)
Tetrahedron
, vol.50
, pp. 3349-3362
-
-
Enders, D.1
Schäfer, T.2
Piva, O.3
Zamponi, A.4
-
35
-
-
0030041646
-
-
and references therein
-
(b) Enders, D.; Piva, O.; Burkamp, F. Tetrahedron 1996, 52, 2893-2908 and references therein.
-
(1996)
Tetrahedron
, vol.52
, pp. 2893-2908
-
-
Enders, D.1
Piva, O.2
Burkamp, F.3
-
36
-
-
0000687379
-
-
(a) Evans, D. A; Ellman, J. A.; Dorow, R. L. Tetrahedron Lett. 1987, 28, 1123-1126.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 1123-1126
-
-
Evans, D.A.1
Ellman, J.A.2
Dorow, R.L.3
-
37
-
-
0025324609
-
-
(b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 4011-4030
-
-
Evans, D.A.1
Britton, T.C.2
Ellman, J.A.3
Dorow, R.L.4
-
38
-
-
0343418810
-
-
note
-
When the reductive cleavage was attempted on the α-arylthioimide derived from 3,3-dimethylbutanoic acid, reaction was only observed at the endocyclic carbonyl.
-
-
-
-
40
-
-
0342983402
-
-
note
-
For β-hydroxy sulfides containing an S-benzyl substituent, the product derived from anti-Felkin-controlled addition was the major diastereomer.
-
-
-
-
41
-
-
33845376028
-
-
The relative stereochemistry was determined by analysis of the O-methylmandelate esters according to the method of: Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374.
-
(1986)
J. Org. Chem.
, vol.51
, pp. 2370-2374
-
-
Trost, B.M.1
Belletire, J.L.2
Godleski, S.3
McDougal, P.G.4
Balkovec, J.M.5
Baldwin, J.J.6
Christy, M.E.7
Ponticello, G.S.8
Varga, S.L.9
Springer, J.P.10
-
42
-
-
0343854678
-
-
Reference 5b
-
(a) Reference 5b.
-
-
-
-
44
-
-
0028882906
-
-
(c) Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kuhnle, F.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta 1995, 78, 1636-1650.
-
(1995)
Helv. Chim. Acta
, vol.78
, pp. 1636-1650
-
-
Seebach, D.1
Devaquet, E.2
Ernst, A.3
Hayakawa, M.4
Kuhnle, F.5
Schweizer, W.B.6
Weber, B.7
-
45
-
-
0001158709
-
-
Rebeiere, F.; Samuel, O.; Ricard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991-5999.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 5991-5999
-
-
Rebeiere, F.1
Samuel, O.2
Ricard, L.3
Kagan, H.B.4
-
46
-
-
0026512681
-
-
Casey, M.; Mukherjee, I.; Trabsa, H. Tetrahedron Lett. 1992, 33, 127-130.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 127-130
-
-
Casey, M.1
Mukherjee, I.2
Trabsa, H.3
-
47
-
-
0342549028
-
-
note
-
A similar ratio was obtained when benzaldehyde was used (20k: 21k = 1:1), but some selectivity was observed when isobutyraldehyde was employed (22k:23k = 1:3).
-
-
-
-
48
-
-
0030853206
-
-
(a) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108-2110.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2108-2110
-
-
Steinhagen, H.1
Reggelin, M.2
Helmchen, G.3
-
49
-
-
0028349296
-
-
(b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-1526.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 1523-1526
-
-
Sprinz, J.1
Kiefer, M.2
Helmchen, G.3
Reggelin, M.4
Huttner, G.5
Walter, O.6
Zsolnai, L.7
-
50
-
-
0029928380
-
-
(c) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 1031-1037
-
-
Togni, A.1
Burckhardt, U.2
Gramlich, V.3
Pregosin, P.S.4
Salzmann, R.5
-
52
-
-
0343418803
-
-
note
-
Lowering of the temperature below -20 °C caused the reactions to stall at 75% conversion and no increase in the enantioselectivity.
-
-
-
-
53
-
-
33748227479
-
-
(a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 566-568
-
-
Von Matt, P.1
Pfaltz, A.2
-
55
-
-
0029928975
-
-
(c) Trost, B. M.; Krueger, A. C.; Bunt, R.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520-6521.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 6520-6521
-
-
Trost, B.M.1
Krueger, A.C.2
Bunt, R.3
Zambrano, J.4
-
56
-
-
0001638084
-
-
For analogous allylic aminations see: (d) Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191-193.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 191-193
-
-
Hayashi, T.1
Yamamoto, A.2
Hagihara, T.3
Ito, Y.4
-
57
-
-
0342983398
-
-
note
-
It was believed that a more sterically demanding chiral pocket would increase the enantiomeric excess observed in the alkylation of 1,3-dimethylpropenyl acetate; however, using ligands containing bulkier phosphine substituents (33f and 33g) resulted in significantly lower enantioselectivities, 14% ee and 49% ee, respectively.
-
-
-
-
58
-
-
33845378604
-
-
These substrates were reported to afford exclusive alkylation at the less substituted terminus. (a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046. (b) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535-2546 and references therein.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 2033-2046
-
-
Auburn, P.R.1
Mackenzie, P.B.2
Bosnich, B.3
-
59
-
-
0028882941
-
-
and references therein
-
These substrates were reported to afford exclusive alkylation at the less substituted terminus. (a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046. (b) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535-2546 and references therein.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 2535-2546
-
-
Dawson, G.J.1
Williams, J.M.J.2
Coote, S.J.3
-
60
-
-
0343418802
-
-
note
-
In contrast to most of the previously described allylic alkylations, these reactions showed no conversion at temperatures lower than room temperature.
-
-
-
-
61
-
-
0342983396
-
-
note
-
No product was observed in the allylic alkylation of 34d.
-
-
-
-
62
-
-
0030984990
-
-
Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783-4784. Separation of enantiomers on the corresponding benzoate ester by HPLC analysis (Daicel Chiralcel AD) determined the enantiomeric excess to be >99%.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4783-4784
-
-
Iida, T.1
Yamamoto, N.2
Sasai, H.3
Shibasaki, M.4
-
63
-
-
0343854666
-
-
note
-
1; a = 12.4686
-
-
-
-
64
-
-
0342549020
-
-
note
-
3; Z = 4; R = 0.0627, GoF = 1.019.
-
-
-
-
65
-
-
84987460614
-
-
For an example of an X-ray crystal structuce of a single diastereomeric complex showing two diastereomers in solution by NMR, see: Berger, H.; Nesper, R.; Pregosin, P. S.; Rüegger, H.; Wörle, M. Helv. Chim. Acta 1993, 76, 1520-1538.
-
(1993)
Helv. Chim. Acta
, vol.76
, pp. 1520-1538
-
-
Berger, H.1
Nesper, R.2
Pregosin, P.S.3
Rüegger, H.4
Wörle, M.5
-
66
-
-
85049056494
-
-
For an excellent reveiew on the structure and dynamics of chiral allyl complexes of Pd(II) see: Pregosin, P. S.; Salimann, R. Coord. Chem. Rev. 1996, 96, 35-68.
-
(1996)
Coord. Chem. Rev.
, vol.96
, pp. 35-68
-
-
Pregosin, P.S.1
Salimann, R.2
-
67
-
-
0343854663
-
-
note
-
3; Z = 4; R = 0.0386, GoF = 0.974.
-
-
-
-
68
-
-
3743127668
-
-
Strongly rotated allyl moieties have been reported in crystal structures of various mixed donor ligand-palladium π-allyl complexes. (a) Albinati, A.; Pregosin, P. S.; Wick, K. Organometallics 1996, 15, 2419-21. (b) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (c) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-6.
-
(1996)
Organometallics
, vol.15
, pp. 2419-2421
-
-
Albinati, A.1
Pregosin, P.S.2
Wick, K.3
-
69
-
-
0029928380
-
-
Strongly rotated allyl moieties have been reported in crystal structures of various mixed donor ligand-palladium π-allyl complexes. (a) Albinati, A.; Pregosin, P. S.; Wick, K. Organometallics 1996, 15, 2419- 21. (b) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (c) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-6.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 1031-1037
-
-
Togni, A.1
Burckhardt, U.2
Gramlich, V.3
Pregosin, P.S.4
Salzmann, R.5
-
70
-
-
0028349296
-
-
Strongly rotated allyl moieties have been reported in crystal structures of various mixed donor ligand-palladium π-allyl complexes. (a) Albinati, A.; Pregosin, P. S.; Wick, K. Organometallics 1996, 15, 2419- 21. (b) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (c) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-6.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 1523-1526
-
-
Sprinz, J.1
Kiefer, M.2
Helmchen, G.3
Reggelin, M.4
Huttner, G.5
Walter, O.6
Zsolnai, L.7
-
71
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0343854660
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-
note
-
2 bond between Pd and C2-C3.
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-
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72
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0343418796
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-
note
-
allyl(trans to S) = 5.48 ppm.
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-
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73
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33845379753
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Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046-2054. For a review on Curtin-Hammett kinetics with numerous examples, see: Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 2046-2054
-
-
Mackenzie, P.B.1
Whelan, J.2
Bosnich, B.3
-
74
-
-
1542554559
-
-
Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046-2054. For a review on Curtin-Hammett kinetics with numerous examples, see: Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
-
(1983)
Chem. Rev.
, vol.83
, pp. 83-134
-
-
Seeman, J.I.1
-
75
-
-
0025356808
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-
Although the enantioselective allylic alkylation is difficult to accomplish, the substrate synthesis is quite facile by allylic oxidation of the desired cycloalkene. Hansson, S.; Heumann, A.; Rein, T.; Akermark, B. J. Org. Chem. 1990, 55, 975-984.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 975-984
-
-
Hansson, S.1
Heumann, A.2
Rein, T.3
Akermark, B.4
-
76
-
-
0025874024
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-
While Pd-sparteine complexes catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 75% ee, the corresponding alkylation on cyclohexenyl acetate proceeds in only 50% ee. (a) Togni, A. Tetrahedron: Asymmetry 1991, 2, 683-690. Similarly, chiral phenanthroline complexes were found to catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 92% ee, but the alkylation of cyclohexenyl acetate proceeds in only 16% ee. (b) Pena-Cabrera, E.; Norrby, P.; Sjögren, M.; Vitagliano, A.; de Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299-4313.
-
(1991)
Tetrahedron: Asymmetry
, vol.2
, pp. 683-690
-
-
Togni, A.1
-
77
-
-
0343136162
-
-
While Pd-sparteine complexes catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 75% ee, the corresponding alkylation on cyclohexenyl acetate proceeds in only 50% ee. (a) Togni, A. Tetrahedron: Asymmetry 1991, 2, 683-690. Similarly, chiral phenanthroline complexes were found to catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 92% ee, but the alkylation of cyclohexenyl acetate proceeds in only 16% ee. (b) Pena-Cabrera, E.; Norrby, P.; Sjögren, M.; Vitagliano, A.; de Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299-4313.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 4299-4313
-
-
Pena-Cabrera, E.1
Norrby, P.2
Sjögren, M.3
Vitagliano, A.4
De Felice, V.5
Oslob, J.6
Ishii, S.7
O'Neill, D.8
Akermark, B.9
Helquist, P.10
-
78
-
-
0001036697
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-
The ligands developed by Trost are effective for the allylic alkylation of both cyclic and acyclic substrates; however, only acyclic substrates containing sterically small substituents gave high enantiomeric excesses. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. (b) Knuehl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846 and references therein. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 4089-4090
-
-
Trost, B.M.1
Bunt, R.C.2
-
79
-
-
0001036697
-
-
and references therein
-
The ligands developed by Trost are effective for the allylic alkylation of both cyclic and acyclic substrates; however, only acyclic substrates containing sterically small substituents gave high enantiomeric excesses. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. (b) Knuehl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846 and references therein. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
-
(1995)
J. Chem. Soc., Chem. Commun.
, pp. 1845-1846
-
-
Knuehl, G.1
Sennhenn, P.2
Helmchen, G.3
-
80
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0032538768
-
-
The ligands developed by Trost are effective for the allylic alkylation of both cyclic and acyclic substrates; however, only acyclic substrates containing sterically small substituents gave high enantiomeric excesses. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. (b) Knuehl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846 and references therein. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
-
(1998)
Angew. Chem., Int. Ed. Engl.
, vol.37
, pp. 3047-3050
-
-
Kudis, S.1
Helmchen, G.2
-
81
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0342983384
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note
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2 as the nucleophile in THF afforded good yields of 55a in 58% and 89% ee, respectively.
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-
-
-
82
-
-
1642324310
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-
Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 9327-9343
-
-
Trost, B.M.1
Van Vranken, D.L.2
Bingel, C.3
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83
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0343854651
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-
note
-
When ligands 10k and 11k were used in the allylic alkylation of 1,4-diacetoxycyclopentene, the monoalkylated adduct was obtained in 91% and 62% ee, respectively.
-
-
-
-
84
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0001164165
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The most notable exception is the asymmetric palladium-catalyzed allylic substitution of cis-2,5-diacyloxy-2,5-dihydrofuran toward the synthesis of nucleosides. Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037-3038,
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 3037-3038
-
-
Trost, B.M.1
Shi, Z.2
-
85
-
-
0343854647
-
-
and references therein
-
Hoveyda, A. Top. Organomet. Chem. 1998, 1, 106-132 and references therein.
-
(1998)
Top. Organomet. Chem.
, vol.1
, pp. 106-132
-
-
Hoveyda, A.1
-
87
-
-
0030994105
-
-
and references cited therein
-
Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897 and references cited therein.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 3887-3897
-
-
Dias, E.L.1
Nguyen, S.T.2
Grubbs, R.H.3
-
88
-
-
0001428512
-
-
and references therein
-
2,6-Diisopropylphenylimidoneophylidenemolybdenum(VI) bis(hexafluoro-tert-butoxide). Schrock, R. R. Pure Appl. Chem. 1994, 66, 1447-1454 and references therein.
-
(1994)
Pure Appl. Chem.
, vol.66
, pp. 1447-1454
-
-
Schrock, R.R.1
-
89
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-
0343418791
-
-
note
-
3; Z = 4; R = 0.0433, GoF = 1.282.
-
-
-
-
90
-
-
0343418783
-
-
note
-
C1-C2 is shorter (1.36 Å) than C2-C3 (1.44 Å).
-
-
-
-
91
-
-
0342983375
-
-
note
-
Geometry optimizations were performed at the PM3(tm) level using the Spartan Semiempirical Program 5.0 (Wavefunction Inc., Irvine, CA 92715) on a Silicon Graphics Impact 10000 (195 MHz, 128 M RAM) running IRIX 6.2. Calculations ere performed without counterions or solvent using these parameters: optcycle = 2000, maxcycle = 2000, charge = 0, multiplicity = 0. Calculations converged (energy difference between cycles <0.0005 kcal/mol) in ≤4 h CPU time.
-
-
-
-
92
-
-
0343418790
-
-
note
-
2 is small (<1.0 kcal/mol), making it difficult to (fetermine the nature of the drastic difference in the observed enantioselectivities in the allylic substitution of both acyclic and cyclic substrates.
-
-
-
-
93
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0000868533
-
-
The most notable example of a minor diastereomeric complex reacting faster than the major was reported by Halpem in the rhodium-catalyzed hydrogenation of (Z)-acetamidocinnamates. (a) Halpern, J. Science 1982, 217, 401 -407. (b) Halpern, J.; Landis, C. R. J. Am. Chem. Soc. 1987, 109, 1746-1754 and references therein.
-
(1982)
Science
, vol.217
, pp. 401-407
-
-
Halpern, J.1
-
94
-
-
33845281011
-
-
and references therein
-
The most notable example of a minor diastereomeric complex reacting faster than the major was reported by Halpem in the rhodium- catalyzed hydrogenation of (Z)-acetamidocinnamates. (a) Halpern, J. Science 1982, 217, 401 -407. (b) Halpern, J.; Landis, C. R. J. Am. Chem. Soc. 1987, 109, 1746-1754 and references therein.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 1746-1754
-
-
Halpern, J.1
Landis, C.R.2
-
97
-
-
0030984990
-
-
Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783-4784.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4783-4784
-
-
Iida, T.1
Yamamoto, N.2
Sasai, H.3
Shibasaki, M.4
-
99
-
-
33845183545
-
-
Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Muira, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301-6311.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 6301-6311
-
-
Hayashi, T.1
Yamamoto, A.2
Ito, Y.3
Nishioka, E.4
Muira, H.5
Yanagi, K.6
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