-
2
-
-
85007136055
-
-
(Eds.: H. Baltes, W Göpel, J. Hesse), Elsevier, Amsterdam, For classical reviews, see
-
b)T.V. Hansen, Y. StenstrØm in Organic Synthesis: Theory and Applications, Vol 5 (Eds.: H. Baltes, W Göpel, J. Hesse), Elsevier, Amsterdam, 1996, pp. 1-38. For classical reviews, see:
-
(1996)
Organic Synthesis: Theory and Applications
, vol.5
, pp. 1-38
-
-
Hansen, T.V.1
Stenstrøm, Y.2
-
9
-
-
0041009142
-
-
Thieme, Stuttgart
-
b) A. de Meijere, in Carbocyclic Four-Membered Ring Compounds, Houben-Weyl, Methods of Organic Chemistry, vol. 17f, Thieme, Stuttgart, 1997;
-
(1997)
Carbocyclic Four-Membered Ring Compounds, Houben-Weyl, Methods of Organic Chemistry
, vol.17 F
-
-
De Meijere, A.1
-
10
-
-
77953828769
-
-
(Eds. : A. Albini, M. Fagnoni), Wiley-VCH, Weinheim
-
c)I P. Hehn, C. Müller, T. Bach in Handbook of Synthetic Photochemistry (Eds. : A. Albini, M. Fagnoni), Wiley-VCH, Weinheim, 2009, pp. 171-215;
-
(2009)
Handbook of Synthetic Photochemistry
, pp. 171-215
-
-
Hehn, I.P.1
Müller, C.2
Bach, T.3
-
12
-
-
77955312557
-
-
For representative transitionmetal-catalyzed reactions that can lead to cyclobutene products, see
-
For representative transitionmetal-catalyzed reactions that can lead to cyclobutene products, see:
-
-
-
-
13
-
-
20444496467
-
-
e) A, Fürstner, P. W Davies, T. Gress, J Am. Chem. Soc. 2005, 727,8244-8245;
-
(2005)
J Am. Chem. Soc.
, vol.727
, pp. 8244-8245
-
-
Fürstner, A.1
Davies, P.W.2
Gress, T.3
-
14
-
-
33745042632
-
-
f) M. Shi, L. P. Liu, I Tang, J. Am. Chem. Soc. 2006, 72S, 7430-7431;
-
(2006)
J. Am. Chem. Soc.
, vol.72 S
, pp. 7430-7431
-
-
Shi, M.1
Liu, L.P.2
Tang, I.3
-
17
-
-
77953175284
-
-
i) Y. T. Lee, T. K. Kang, Y. K. Chung, J. Org. Chem. 2009, 74, 7922-7934, and references therein.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 7922-7934
-
-
Lee, Y.T.1
Kang, T.K.2
Chung, Y.K.3
-
18
-
-
0001018735
-
-
For the isolation, of these compounds, see: grandisol: a) IH. Tumlinson, D. D. Hardee, R. C. Gueldner, A. C. Thompson, P.A. Hedin, IP. Minyard, Science 1969, 766, 1010-1012; unnamed illudane:
-
(1969)
Science
, vol.766
, pp. 1010-1012
-
-
Tumlinson, I.H.1
Hardee, D.D.2
Gueldner, R.C.3
Thompson, A.C.4
Hedin, P.A.5
Minyard, I.P.6
-
19
-
-
84936230181
-
-
illudosin
-
b) F. Bohlmann, M. Grenz, P. Wegner, I Jakupovic, Liebigs Ann. Chem. 1983, 2008-2020; illudosin:
-
(1983)
Liebigs Ann. Chem.
, pp. 2008-2020
-
-
Bohlmann, F.1
Grenz, M.2
Wegner, P.3
Jakupovic, I.4
-
20
-
-
77955312902
-
-
pestalotiopsin A
-
c) A. Amone, R. Cardillo, G. Nasini, O. V. de Pava, J. Chem. Soc. Perkin Trans. 11991,1787-1791; pestalotiopsin A:
-
(1991)
J. Chem. Soc. Perkin Trans.1
, pp. 1787-1791
-
-
Amone, A.1
Cardillo, R.2
Nasini, G.3
De Pava, O.V.4
-
21
-
-
0029877241
-
-
d) M. Pulici, F. Sugawara, H. Koshino, I Uzawa, S. Yoshida, E., Lobkovsky, I Clardy, J. Org. Chem. 1996, 67, 2122-2124.
-
(1996)
J. Org. Chem.
, vol.67
, pp. 2122-2124
-
-
Pulici, M.1
Sugawara, F.2
Koshino, H.3
Uzawa, I.4
Yoshida, S.5
Lobkovsky, E.6
Clardy, I.7
-
22
-
-
0242666167
-
-
For related examples of [2+2] alkyne/enone or haloolefin/enone cycloadditions, see: a) I D. White, M. A. Avery, IP. Carter, J. Am. Chem. Soc. 1982,104, 5486-5489;
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 5486-5489
-
-
White, I.D.1
Avery, M.A.2
Carter, I.P.3
-
23
-
-
0034644425
-
-
b) J. D. White, I Kim, N. E. Drápela, J. Am. Chem. Soc. 2000,122, 8665-8671;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8665-8671
-
-
White, J.D.1
Kim, I.2
Drápela, N.E.3
-
25
-
-
0043236240
-
-
d) M. Inoue, T. Sato, M. Hirama, / Am. Chem. Soc. 2003, 125,10772-10773;
-
(2003)
Am. Chem. Soc.
, vol.125
, pp. 10772-10773
-
-
Inoue, M.1
Sato, T.2
Hirama, M.3
-
26
-
-
2442436758
-
-
e)R. Alibés, P. de March, M. Figueredo, I Font, M. Racamonde, T. Parella, Org. Lett. 2004, 6,1449-1452.
-
(2004)
Org. Lett.
, vol.6
, pp. 1449-1452
-
-
Alibés, R.1
De March, P.2
Figueredo, M.3
Font, I.4
Racamonde, M.5
Parella, T.6
-
28
-
-
0030069041
-
-
b) F. Binns, R. Hayes, K.J. Hodgetts, S. T. Saengchantara, T. W. Wallace, C. J. Wallis, Tetrahedron 1996,52, 3631-3658;
-
(1996)
Tetrahedron
, vol.52
, pp. 3631-3658
-
-
Binns, F.1
Hayes, R.2
Hodgetts, K.J.3
Saengchantara, S.T.4
Wallace, T.W.5
Wallis, C.J.6
-
29
-
-
0033548151
-
-
c) M.-E. Gourdel-Martin, C. Comoy, F. Huet, Tetrahedron: Asymmetry 1999, 10, 403-404;
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 403-404
-
-
Gourdel-Martin, M.-E.1
Comoy, C.2
Huet, F.3
-
31
-
-
68949122370
-
-
e) S. Ogawa, D. Urabe, Y. Yokokura, H. Arai, M. Arita, M. Inoue, Org. Lett. 2009,77,3602-3605.
-
(2009)
Org. Lett.
, vol.77
, pp. 3602-3605
-
-
Ogawa, S.1
Urabe, D.2
Yokokura, Y.3
Arai, H.4
Arita, M.5
Inoue, M.6
-
32
-
-
0001488571
-
-
For further studies on the photochemical conversion of 2 to 3, see
-
a) E. I Corey, I Streith, J. Am. Chem. Soc. 1964, 86, 950-951. For further studies on the photochemical conversion of 2 to 3, see:
-
(1964)
J. Am. Chem. Soc.
, vol.86
, pp. 950-951
-
-
Corey, E.I.1
Streith, I.2
-
34
-
-
0345931393
-
-
c) W. H. Pirkle, L. H. McKendry, 7. Am. Chem. Soc. 1969,91,1,179-1186;
-
(1969)
J. Am. Chem. Soc.
, vol.91
, Issue.1
, pp. 179-1186
-
-
Pirkle, W.H.1
McKendry, L.H.2
-
35
-
-
0003274053
-
-
d) B. R. Arnold, C. E. Brown,I Lusztyk, J. Am. Chem. Soc. 1993, 115,1576-1577.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 1576-1577
-
-
Arnold, B.R.1
Brown, C.E.2
Lusztyk, I.3
-
36
-
-
77955337674
-
-
To our knowledge, only one report of the lactone opening of 3 (by the use of concentrated HCl; no yields reported) has appeared in the literature; see reference [7b]
-
To our knowledge, only one report of the lactone opening of 3 (by the use of concentrated HCl; no yields reported) has appeared in the literature; see reference [7b].
-
-
-
-
37
-
-
77955332610
-
-
For details, see the Supporting Information.
-
For details, see the Supporting Information.
-
-
-
-
38
-
-
0000969879
-
-
Wiley, New York, chap. 4
-
For leading references of palladium-catalyzed allylic alkylation, see: a) I Tsuji in Palladium Reagents and Catalysts, Wiley, New York, 1996, chap. 4, pp. 290-404;
-
(1996)
Palladium Reagents and Catalysts
, pp. 290-404
-
-
Tsuji, I.1
-
39
-
-
77955313367
-
-
b) C. G. Frost, I Howarth, J. M. I Williams, Tetrahedron: Asymmetry 1992, 31,089-1122;
-
(1992)
Tetrahedron: Asymmetry
, vol.31
, pp. 089-1122
-
-
Frost, C.G.1
Howarth, I.2
Williams, J.M.I.3
-
40
-
-
0003544583
-
-
(Ed.: I. Ojima), VCH Publishers, New York
-
c) T. Hayashi in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH Publishers, New York, 1993, p. 325;
-
(1993)
Catalytic Asymmetric Synthesis
, pp. 325
-
-
Hayashi, T.1
-
42
-
-
77955335330
-
-
See the Supporting Information.
-
See the Supporting Information.
-
-
-
-
43
-
-
77955336503
-
-
The structures of 4a and 7a were confirmed by single-crystal Xray analysis (see the Supporting Information for details). CCDC 765516 (4a) and CCDC 76551,7 (7a) contain the supplementary crystallographic data for this paper. These data can, be obtained free of charge from The Cambridge Crystallographic Data Centre via
-
The structures of 4a and 7a were confirmed by single-crystal Xray analysis (see the Supporting Information for details). CCDC 765516 (4a) and CCDC 76551,7 (7a) contain the supplementary crystallographic data for this paper. These data can, be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datajequest/cif.
-
-
-
-
44
-
-
0033601122
-
-
references cited therein, For reviews on a,a-disubstituted (quaternary) a-amino acids see
-
For the use of a.a-disubstituted (quaternary) a-amino acids in peptidomimetics see: a) B. M. Trost, X. Ariza,7. Am. Chem. Soc. 1,999, 727, 10727-10737 references cited therein, For reviews on a,a-disubstituted (quaternary) a-amino acids see:
-
(1999)
J. Am. Chem. Soc.
, vol.727
, pp. 10727-10737
-
-
Trost, B.M.1
Ariza, X.2
-
49
-
-
51749120761
-
-
For a loosely related transformation, see: S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, K. A. Jorgensen, J. Am. Chem. Soc. 2008, 130,12031-12037.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 12031-12037
-
-
Cabrera, S.1
Reyes, E.2
Alemán, J.3
Milelli, A.4
Kobbelgaard, S.5
Jorgensen, K.A.6
-
50
-
-
0035852114
-
-
3)J, by Trost and Lee in a related example. See
-
3)J, by Trost and Lee in a related example. See: B. M. Trost, C. Lee, J. Am. Chem. Soc. 2001, 725, ,1,21,91-12201.
-
(2001)
J. Am. Chem. Soc.
, vol.725
, pp. 12191-12201
-
-
Trost, B.M.1
Lee, C.2
-
51
-
-
77955317891
-
-
The precise origin of this unprecedented effect is not clear.
-
The precise origin of this unprecedented effect is not clear.
-
-
-
-
52
-
-
0034622921
-
-
For selected references on cyclobutane amino acids, see: a) M. Martin-Vila, E. Muray, G. P. Aguado, A. Alvarez-Larena, V. Branchadell, C. Minguillón, E, Giralt, R. M. Ortuño, Tetrahedron: Asymmetry 2000, 77, 3569-3584;
-
(2000)
Tetrahedron: Asymmetry
, vol.77
, pp. 3569-3584
-
-
Martin-Vila, M.1
Muray, E.2
Aguado, G.P.3
Alvarez-Larena, A.4
Branchadell, V.5
Minguillón, C.6
Giralt, E.7
Ortuño, R.M.8
-
53
-
-
25444510687
-
-
b) S. Izquierdo, F. Rúa, A. Sbai, T. Parella, A. Alvarez-Larena, V. Branchadell, R. M. Ortuño, J. Org. Chem. 2005, 70, 7963-7971;
-
(2005)
J. Org. Chem.
, vol.70
, pp. 7963-7971
-
-
Izquierdo, S.1
Rúa, F.2
Sbai, A.3
Parella, T.4
Alvarez-Larena, A.5
Branchadell, V.6
Ortuño, R.M.7
-
54
-
-
1242338114
-
-
c) D. J. Aitken, C. Gauzy, E. Pereira, Tetrahedron Lett. 2004, 45, 2359-2361;
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 2359-2361
-
-
Aitken, D.J.1
Gauzy, C.2
Pereira, E.3
-
55
-
-
11844273833
-
-
d) A. Avenoza, I H. Busto, N. Canal, I M. Peregrina, J. Org. Chem. 2005, 70, 330-333;
-
(2005)
J. Org. Chem.
, vol.70
, pp. 330-333
-
-
Avenoza, A.1
Busto, I.H.2
Canal, N.3
Peregrina, I.M.4
-
56
-
-
37249016590
-
-
e) A. Mondière, R. Peng, R. Remuson, D. I Aitken, Tetrahedron 2008, 64, 1088-1093;
-
(2008)
Tetrahedron
, vol.64
, pp. 1088-1093
-
-
Mondière, A.1
Peng, R.2
Remuson, R.3
Aitken, D.I.4
-
57
-
-
66149190560
-
-
f) E. Torres, E. Gorrea, E. Da Silva, P. Nolis, V. Branchadell, R. M. Ortuño, Org. Lett. 2009, 11, 2301-2304;
-
(2009)
Org. Lett.
, vol.11
, pp. 2301-2304
-
-
Torres, E.1
Gorrea, E.2
Da Silva, E.3
Nolis, P.4
Branchadell, V.5
Ortuño, R.M.6
-
58
-
-
28044470527
-
-
For cyclobutene nucleosides, see
-
g) B. Basier, O. Schuster, T. Bach, J. Org. Chem. 2005, 70, 9798-9808. For cyclobutene nucleosides, see:
-
(2005)
J. Org. Chem.
, vol.70
, pp. 9798-9808
-
-
Basier, B.1
Schuster, O.2
Bach, T.3
-
59
-
-
0030921946
-
-
For cyclobutene analogues of acetylcholine, see
-
h) M.-E. Gourdel-Martin, F. Huet, J. Org. Chem. 1997, 62, 2166-2172. For cyclobutene analogues of acetylcholine, see:
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2166-2172
-
-
Gourdel-Martin, M.-E.1
Huet, F.2
-
60
-
-
0020336327
-
-
i) J. G. Cannon, D. M. Crockatt, J. P. Long, W. Maixner, J. Med. Chem. 1982, 25,1091-1094.
-
(1982)
J. Med. Chem.
, vol.25
, pp. 1091-1094
-
-
Cannon, J.G.1
Crockatt, D.M.2
Long, J.P.3
Maixner, W.4
-
61
-
-
65949124477
-
-
For selected references, see: a) R. O. Jeon, D. Rayabarapu, A. Rolfe, K. Volp, I. Omar, P. R. Hanson, Tetrahedron 2009, 65, 4992-5000;
-
(2009)
Tetrahedron
, vol.65
, pp. 4992-5000
-
-
Jeon, R.O.1
Rayabarapu, D.2
Rolfe, A.3
Volp, K.4
Omar, I.5
Hanson, P.R.6
-
63
-
-
0037048460
-
-
c) H. Ovaa, C. Stapper, G. A. van der Marel, H. S. Overkleeft, I H. van Boom, S. Blechert, Tetrahedron 2002, 55,7503-7518.
-
(2002)
Tetrahedron
, vol.55
, pp. 7503-7518
-
-
Ovaa, H.1
Stapper, C.2
Van Der Marel, G.A.3
Overkleeft, H.S.4
Van Boom, I.H.5
Blechert, S.6
-
65
-
-
19744375818
-
-
b) J. Clayden, B. Read, K. R. Hebditch, Tetrahedron 2005,67,5713-5724.
-
(2005)
Tetrahedron
, vol.67
, pp. 5713-5724
-
-
Clayden, J.1
Read, B.2
Hebditch, K.R.3
-
66
-
-
0042318784
-
-
For selected synthetic studies on, Pestalotiopsin A, see: a) D. Johnston, E. Couché, D. J. Edmonds, K. W. Muir, D. I Procter, Org. Biomol Chem. 2003, 7, 328-337;
-
(2003)
Org. Biomol Chem.
, vol.7
, pp. 328-337
-
-
Johnston, D.1
Couché, E.2
Edmonds, D.J.3
Muir, K.W.4
Procter, D.I.5
-
67
-
-
70349958038
-
-
b)T. M. Baker, D.J. Edmonds, D. Hamilton, C. I O'Brien, D. I Procter, Angew. Chem. 2008, 720, 5713-5715;
-
(2008)
Angew. Chem.
, vol.720
, pp. 5713-5715
-
-
Baker, T.M.1
Edmonds, D.J.2
Hamilton, D.3
O'Brien, C.I.4
Procter, D.I.5
-
68
-
-
49649117978
-
-
Angew. Chem. Int. Ed. 2008, 47, 5631-5633;
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 5631-5633
-
-
-
69
-
-
34548727336
-
-
c) L. A. Paquette, G. D. Parker, T. Tei, S. Dong, J. Org. Chem. 2007, 72, 7125-7134;
-
(2007)
J. Org. Chem.
, vol.72
, pp. 7125-7134
-
-
Paquette, L.A.1
Parker, G.D.2
Tei, T.3
Dong, S.4
-
70
-
-
34548707029
-
-
For the only completed total synthesis to date, see
-
d) L. A. Paquette, S. Dong, G. D. Parker, J. Org. Chem. 2007, 72, 7135-7147. For the only completed total synthesis to date, see:
-
(2007)
J. Org. Chem.
, vol.72
, pp. 7135-7147
-
-
Paquette, L.A.1
Dong, S.2
Parker, G.D.3
-
71
-
-
53549130350
-
-
e) K. Takao, N. Hayakawa, R, Yamada, T. Yamaguchi, U. Morita, S. Kawasaki, K.-i. Tadano, Angew. Chem. 2008,720,3474-3477;
-
(2008)
Angew. Chem.
, vol.720
, pp. 3474-3477
-
-
Takao, K.1
Hayakawa, N.2
Yamada, R.3
Yamaguchi, T.4
Morita, U.5
Kawasaki, S.6
Tadano, K.-I.7
-
72
-
-
43849098048
-
-
Angew. Chem. Int. Ed. 2008, 47, 3426-3429.
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 3426-3429
-
-
-
73
-
-
0029103383
-
-
This is quite likely an instance of type-II Dynamic Kinetic Asymmetric Transformation (DYKAT). For general reviews about Dynamic Kinetic Resolution, see: a
-
This is quite likely an instance of type-II Dynamic Kinetic Asymmetric Transformation (DYKAT). For general reviews about Dynamic Kinetic Resolution, see: a) R. S. Ward, Tetrahedron: Asymmetry 1995, 6,1475-1490;
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 1475-1490
-
-
Ward, R.S.1
-
74
-
-
77955310224
-
-
For a specific review about Pd and DYKAT, see
-
b) H. Pellissier, Tetrahedron 2003, 59, 8921-8927. For a specific review about Pd and DYKAT, see:
-
(2003)
Tetrahedron
, vol.59
, pp. 8921-8927
-
-
Pellissier, H.1
-
75
-
-
35048857286
-
-
For an excellent, scholarly classification of all possible DYKAT modes, see
-
c) B. M. Trost, D. R. Fandrick, Aldrichimica Acta 2007, 40, 59-72. For an excellent, scholarly classification of all possible DYKAT modes, see:
-
(2007)
Aldrichimica Acta
, vol.40
, pp. 59-72
-
-
Trost, B.M.1
Fandrick, D.R.2
-
76
-
-
53849089968
-
-
d) I Steinreiber, K. Faber, H. Grieng, Chem. Eur. J. 2008,14, 8060-8072.
-
(2008)
Chem. Eur. J.
, vol.14
, pp. 8060-8072
-
-
Steinreiber, I.1
Faber, K.2
Grieng, H.3
|