-
6
-
-
0009637246
-
-
(a) Y. Inubushi, Y. Sazaki, Y. Tsuda, B. Yasui, T. Konika, J. Matsumoto, E. Katarao, J. Nakano, Tetrahedron 20 (1964) 2007-2023.
-
(1964)
Tetrahedron
, vol.20
, pp. 2007-2023
-
-
Inubushi, Y.1
Sazaki, Y.2
Tsuda, Y.3
Yasui, B.4
Konika, T.5
Matsumoto, J.6
Katarao, E.7
Nakano, J.8
-
7
-
-
0013780327
-
-
(b) Y. Inubushi, Y. Sazaki, Y. Tsuda, J. Nakano, Tetrahedron Lett. 20 (1965) 1519-1523.
-
(1965)
Tetrahedron Lett.
, vol.20
, pp. 1519-1523
-
-
Inubushi, Y.1
Sazaki, Y.2
Tsuda, Y.3
Nakano, J.4
-
8
-
-
0015511557
-
-
(a) K. Yamada, M. Suzuki, Y. Hayakawa, K. Aoki, H. Nakamura, H. Nagase, Y. Hirata, J. Am. Chem. Soc. 94 (1972) 8278-8280.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 8278-8280
-
-
Yamada, K.1
Suzuki, M.2
Hayakawa, Y.3
Aoki, K.4
Nakamura, H.5
Nagase, H.6
Hirata, Y.7
-
9
-
-
0016373568
-
-
(b) Y. Inubushi, T. Kikushi, T. Ibuka, T. Tanaka, I. Saji, K. Tokane, Chem. Pharm. Bull. 22 (1974) 349-369.
-
(1974)
Chem. Pharm. Bull.
, vol.22
, pp. 349-369
-
-
Inubushi, Y.1
Kikushi, T.2
Ibuka, T.3
Tanaka, T.4
Saji, I.5
Tokane, K.6
-
10
-
-
0016402493
-
-
(c) A.S. Kende, T.J. Bentley, R.A. Mader, D. Ridge, J. Am. Chem. Soc. 96 (1974) 4332-4334.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 4332-4334
-
-
Kende, A.S.1
Bentley, T.J.2
Mader, R.A.3
Ridge, D.4
-
13
-
-
84985591654
-
-
(b) B.M. Trost, A.S. Tasker, G. Ruther, A. Brandes, J. Am. Chem. Soc. 113 (1991) 670-672.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 670-672
-
-
Trost, B.M.1
Tasker, A.S.2
Ruther, G.3
Brandes, A.4
-
14
-
-
0026749040
-
-
(c) C.H. Lee, M. Westling, T. Livinghouse, A.C. Williams, J. Am. Chem. Soc. 114 (1992) 4089-4095.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 4089-4095
-
-
Lee, C.H.1
Westling, M.2
Livinghouse, T.3
Williams, A.C.4
-
15
-
-
0027997696
-
-
(d) M. Mon, N. Uesaka, M. Shibasaki, F. Saitoh, K. Okamura, T. Date, J. Org. Chem. 59 (1994) 5633-5642.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 5633-5642
-
-
Mon, M.1
Uesaka, N.2
Shibasaki, M.3
Saitoh, F.4
Okamura, K.5
Date, T.6
-
16
-
-
0030900204
-
-
(e) C-K. Sha, R-T. Chiu, C-F. Yang, NT. Yao, W-H. Tseng, F-L. Liao, S-L. Wang, J. Am. Chem. Soc. 119 (1997) 4130-4135. Since our first communication, an additional, elegant, synthesis of dendrobine has appeared
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4130-4135
-
-
Sha, C.-K.1
Chiu, R.-T.2
Yang, C.-F.3
Yao, N.T.4
Tseng, W.-H.5
Liao, F.-L.6
Wang, S.-L.7
-
19
-
-
0030955447
-
-
For an interesting study on acyl radical acceptors, and as a leading reference, see: D.P. Curran, U. Diederichsen, M. Palovitch, J. Am. Chem. Soc. 119 (1997) 4797-4804.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4797-4804
-
-
Curran, D.P.1
Diederichsen, U.2
Palovitch, M.3
-
21
-
-
0029049881
-
-
(b) J. Boivin, A.-C. Callier-Dublanchet, B. Quiclet-Sire, A.-M. Schiano, S.Z. Zard, Tetrahedron 51 (1995) 6517-6528.
-
(1995)
Tetrahedron
, vol.51
, pp. 6517-6528
-
-
Boivin, J.1
Callier-Dublanchet, A.-C.2
Quiclet-Sire, B.3
Schiano, A.-M.4
Zard, S.Z.5
-
23
-
-
0003168906
-
-
(d) S.Z. Zard, Synlett (1996) 1148-1154.
-
(1996)
Synlett
, pp. 1148-1154
-
-
Zard, S.Z.1
-
27
-
-
0033484123
-
-
The introduction of a cis-vicinal amino alcohol functionality is generally more challenging than for the trans isomer. See: (a) S. Knapp, Chem. Soc. Rev. 28 (1999) 61-72. Interesting compounds in this class include the aminocyclitols (e.g. (+)-valienamine), the aminocyclopentitols (e.g. (+)-mannostatin), or the conduramines. (b) M. Balci, Y. Sutbeyaz, H. Secen, Tetrahedron 49 (1993) 8039-8058. (c) T. Posternak, The Cyclitols, Holden- Day Inc., San Francisco, 1965. (d) B.M. Trost, D.L. Van Vranken, J. Am. Chem. Soc. 115 (1993) 444-458.
-
(1999)
Chem. Soc. Rev.
, vol.28
, pp. 61-72
-
-
Knapp, S.1
-
28
-
-
0033484123
-
-
The introduction of a cis-vicinal amino alcohol functionality is generally more challenging than for the trans isomer. See: (a) S. Knapp, Chem. Soc. Rev. 28 (1999) 61-72. Interesting compounds in this class include the aminocyclitols (e.g. (+)-valienamine), the aminocyclopentitols (e.g. (+)-mannostatin), or the conduramines. (b) M. Balci, Y. Sutbeyaz, H. Secen, Tetrahedron 49 (1993) 8039-8058. (c) T. Posternak, The Cyclitols, Holden- Day Inc., San Francisco, 1965. (d) B.M. Trost, D.L. Van Vranken, J. Am. Chem. Soc. 115 (1993) 444-458.
-
(1993)
Tetrahedron
, vol.49
, pp. 8039-8058
-
-
Balci, M.1
Sutbeyaz, Y.2
Secen, H.3
-
29
-
-
0033484123
-
-
Holden-Day Inc., San Francisco
-
The introduction of a cis-vicinal amino alcohol functionality is generally more challenging than for the trans isomer. See: (a) S. Knapp, Chem. Soc. Rev. 28 (1999) 61-72. Interesting compounds in this class include the aminocyclitols (e.g. (+)-valienamine), the aminocyclopentitols (e.g. (+)-mannostatin), or the conduramines. (b) M. Balci, Y. Sutbeyaz, H. Secen, Tetrahedron 49 (1993) 8039-8058. (c) T. Posternak, The Cyclitols, Holden-Day Inc., San Francisco, 1965. (d) B.M. Trost, D.L. Van Vranken, J. Am. Chem. Soc. 115 (1993) 444-458.
-
(1965)
The Cyclitols
-
-
Posternak, T.1
-
30
-
-
0347584753
-
-
The introduction of a cis-vicinal amino alcohol functionality is generally more challenging than for the trans isomer. See: (a) S. Knapp, Chem. Soc. Rev. 28 (1999) 61-72. Interesting compounds in this class include the aminocyclitols (e.g. (+)-valienamine), the aminocyclopentitols (e.g. (+)-mannostatin), or the conduramines. (b) M. Balci, Y. Sutbeyaz, H. Secen, Tetrahedron 49 (1993) 8039-8058. (c) T. Posternak, The Cyclitols, Holden- Day Inc., San Francisco, 1965. (d) B.M. Trost, D.L. Van Vranken, J. Am. Chem. Soc. 115 (1993) 444-458.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 444-458
-
-
Trost, B.M.1
Van Vranken, D.L.2
-
33
-
-
0032510183
-
-
(c) J. Cassayre, B. Quiclet-Sire, J.-B. Saunier, S.Z. Zard, Tetrahedron 54 (1998) 1029-1040.
-
(1998)
Tetrahedron
, vol.54
, pp. 1029-1040
-
-
Cassayre, J.1
Quiclet-Sire, B.2
Saunier, J.-B.3
Zard, S.Z.4
-
34
-
-
0032481029
-
-
(a) J. Cassayre, B. Quiclet-Sire, J.-B. Saunier, S.Z. Zard, Tetrahedron Lett. 39 (1998) 8995-8998.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 8995-8998
-
-
Cassayre, J.1
Quiclet-Sire, B.2
Saunier, J.-B.3
Zard, S.Z.4
-
36
-
-
0034127044
-
-
We recently reported that the addition of a stoechiometric amount of copper(II) acetate permits the direct oxidation of the final radical, see: J. Cassayre, D. Dauge, S.Z. Zard, Synlett (2000) 471-474.
-
(2000)
Synlett
, pp. 471-474
-
-
Cassayre, J.1
Dauge, D.2
Zard, S.Z.3
-
39
-
-
37049132250
-
-
I.U. Khand,; G.R. Knox, P.L. Pauson, W.E. Watts, M.I. Foreman, J. Chem. Soc. Chem. Commun. (1973( 977-981.
-
(1973)
J. Chem. Soc. Chem. Commun.
, pp. 977-981
-
-
Khand, I.U.1
Knox, G.R.2
Pauson, P.L.3
Watts, W.E.4
Foreman, M.I.5
-
40
-
-
0034686072
-
-
Reviews: (a) K.M. Brummond, Tetrahedron 56 (2000) 3263-3283. (b) O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 37 (1998) 911-914. (c) N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, Oxford, 1991, 1037-1064; (d) N.E. Schore, Org. React. 40 (1991) 1-90. (e) N.E. Schore, Chem. Rev. 88 (1988) 1085-1089. (f) Y.K. Chung, Coord. Chem. Rev. 188 (1999) 297-341. (g) N. Jeong, Trans. Met. Org. Synth. 1 (1998) 3560-577.
-
(2000)
Tetrahedron
, vol.56
, pp. 3263-3283
-
-
Brummond, K.M.1
-
41
-
-
0031971911
-
-
Reviews: (a) K.M. Brummond, Tetrahedron 56 (2000) 3263- 3283. (b) O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 37 (1998) 911-914. (c) N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, Oxford, 1991, 1037-1064; (d) N.E. Schore, Org. React. 40 (1991) 1-90. (e) N.E. Schore, Chem. Rev. 88 (1988) 1085-1089. (f) Y.K. Chung, Coord. Chem. Rev. 188 (1999) 297-341. (g) N. Jeong, Trans. Met. Org. Synth. 1 (1998) 3560-577.
-
(1998)
Angew. Chem. Int. Ed. Engl.
, vol.37
, pp. 911-914
-
-
Geis, O.1
Schmalz, H.-G.2
-
42
-
-
0034686072
-
-
B.M. Trost, I. Fleming (Eds.), Pergamon, Oxford
-
Reviews: (a) K.M. Brummond, Tetrahedron 56 (2000) 3263- 3283. (b) O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 37 (1998) 911-914. (c) N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, Oxford, 1991, 1037-1064; (d) N.E. Schore, Org. React. 40 (1991) 1-90. (e) N.E. Schore, Chem. Rev. 88 (1988) 1085-1089. (f) Y.K. Chung, Coord. Chem. Rev. 188 (1999) 297-341. (g) N. Jeong, Trans. Met. Org. Synth. 1 (1998) 3560-577.
-
(1991)
Comprehensive Organic Synthesis
, vol.5
, pp. 1037-1064
-
-
Schore, N.E.1
-
43
-
-
0034686072
-
-
Reviews: (a) K.M. Brummond, Tetrahedron 56 (2000) 3263- 3283. (b) O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 37 (1998) 911-914. (c) N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, Oxford, 1991, 1037-1064; (d) N.E. Schore, Org. React. 40 (1991) 1-90. (e) N.E. Schore, Chem. Rev. 88 (1988) 1085-1089. (f) Y.K. Chung, Coord. Chem. Rev. 188 (1999) 297-341. (g) N. Jeong, Trans. Met. Org. Synth. 1 (1998) 3560-577.
-
(1991)
Org. React.
, vol.40
, pp. 1-90
-
-
Schore, N.E.1
-
44
-
-
0034686072
-
-
Reviews: (a) K.M. Brummond, Tetrahedron 56 (2000) 3263- 3283. (b) O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 37 (1998) 911-914. (c) N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, Oxford, 1991, 1037-1064; (d) N.E. Schore, Org. React. 40 (1991) 1-90. (e) N.E. Schore, Chem. Rev. 88 (1988) 1085-1089. (f) Y.K. Chung, Coord. Chem. Rev. 188 (1999) 297-341. (g) N. Jeong, Trans. Met. Org. Synth. 1 (1998) 3560-577.
-
(1988)
Chem. Rev.
, vol.88
, pp. 1085-1089
-
-
Schore, N.E.1
-
45
-
-
0000939078
-
-
Reviews: (a) K.M. Brummond, Tetrahedron 56 (2000) 3263- 3283. (b) O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 37 (1998) 911-914. (c) N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, Oxford, 1991, 1037-1064; (d) N.E. Schore, Org. React. 40 (1991) 1-90. (e) N.E. Schore, Chem. Rev. 88 (1988) 1085-1089. (f) Y.K. Chung, Coord. Chem. Rev. 188 (1999) 297-341. (g) N. Jeong, Trans. Met. Org. Synth. 1 (1998) 3560-577.
-
(1999)
Coord. Chem. Rev.
, vol.188
, pp. 297-341
-
-
Chung, Y.K.1
-
46
-
-
0034686072
-
-
Reviews: (a) K.M. Brummond, Tetrahedron 56 (2000) 3263- 3283. (b) O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 37 (1998) 911-914. (c) N.E. Schore, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, Oxford, 1991, 1037-1064; (d) N.E. Schore, Org. React. 40 (1991) 1-90. (e) N.E. Schore, Chem. Rev. 88 (1988) 1085-1089. (f) Y.K. Chung, Coord. Chem. Rev. 188 (1999) 297-341. (g) N. Jeong, Trans. Met. Org. Synth. 1 (1998) 3560-577.
-
(1998)
Trans. Met. Org. Synth.
, vol.1
, pp. 3560-3577
-
-
Jeong, N.1
-
48
-
-
0001731394
-
-
(b) M.F. Krafft, I.L. Scott, R.H. Romero, S. Feibelmann, C.B. Van Pelt, J. Am. Chem. Soc. 115 (1993) 7199-7207.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 7199-7207
-
-
Krafft, M.F.1
Scott, I.L.2
Romero, R.H.3
Feibelmann, S.4
Van Pelt, C.B.5
-
50
-
-
85029867296
-
-
(b) N. Jeong, Y.K. Chung, B.Y. Lee, H.L. Lee, S.-E. Yoo, Synlett (1991) 204-206.
-
(1991)
Synlett
, pp. 204-206
-
-
Jeong, N.1
Chung, Y.K.2
Lee, B.Y.3
Lee, H.L.4
Yoo, S.-E.5
-
51
-
-
0030818489
-
-
As shown in Scheme 9 below, the penultimate intermediate in the Pauson-Khand reaction can undergo the normal reductive elimination to give cyclopentenone 26 or a β-elimination to give 27, perhaps assisted by complexation of the basic nitrogen to a cobalt atom. This hypothesis is supported by similar observations on zirconium-mediated [2 + 2 + 1] cycloadditions of related benzylamines: Ref. [6d] and J. Barluenga, R. Sanz, F. Fananas, Chem. Eur. J. 3 (1997) 1324-1336.
-
(1997)
Chem. Eur. J.
, vol.3
, pp. 1324-1336
-
-
Barluenga, J.1
Sanz, R.2
Fananas, F.3
-
52
-
-
0345196649
-
-
For a study of the influence of coordinating solvents on the Pauson-Khand reaction, see: M.E. Krafft, I.L. Scott, R.H. Romero, S. Feibelmann, C.F. Van Pelt, J. Am. Chem. Soc. 119 (1997) 7199-7207.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 7199-7207
-
-
Krafft, M.E.1
Scott, I.L.2
Romero, R.H.3
Feibelmann, S.4
Van Pelt, C.F.5
-
53
-
-
0032558612
-
-
Without protection of the hydroxy group, the Pauson-Khand reaction proved very sluggish (19% yield) and was accompanied by a large amount of demetallated product (55% yield). For related observations, see: C. Mukai, J.S. Kim, M. Uchiyama, M. Hanaoka, Tetrahedron Lett. 39 (1998) 7909-7912.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 7909-7912
-
-
Mukai, C.1
Kim, J.S.2
Uchiyama, M.3
Hanaoka, M.4
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