-
1
-
-
0000458209
-
-
For a review on substrate-directed reactions, see
-
For a review on substrate-directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
-
(1993)
Chem. Rev.
, vol.93
, pp. 1307
-
-
Hoveyda, A.H.1
Evans, D.A.2
Fu, G.C.3
-
6
-
-
0030909214
-
-
Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 3385
-
-
Singleton, D.A.1
Merrigan, S.R.2
Liu, J.3
Houk, K.N.4
-
7
-
-
0030669437
-
-
Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 10147
-
-
Houk, K.N.1
Liu, J.2
DeMello, N.C.3
Condroski, K.R.4
-
8
-
-
0037013879
-
-
Okovytyy, S.; Gorb, L.; Leszczynski, J. Tetrahedron Lett. 2002, 43, 4215.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 4215
-
-
Okovytyy, S.1
Gorb, L.2
Leszczynski, J.3
-
9
-
-
37049079765
-
-
For a discussion of the stereochemistry of epoxidation in some homoallylic cyclohexene alcohols, see
-
For a discussion of the stereochemistry of epoxidation in some homoallylic cyclohexene alcohols, see: Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759.
-
(1994)
J. Chem. Soc., Perkin Trans. 1
, pp. 1759
-
-
Kočovský, P.1
-
10
-
-
37049128735
-
-
For examples concerning the oxidative functionalization of homoallylic substrates, see ref 1 and
-
For examples concerning the oxidative functionalization of homoallylic substrates, see ref 1 and: Garside, P.; Halsall, T. G.; Hornby, G. M. J. Chem. Soc. C 1969, 716.
-
(1969)
J. Chem. Soc. C
, pp. 716
-
-
Garside, P.1
Halsall, T.G.2
Hornby, G.M.3
-
11
-
-
0001609736
-
-
Ye, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Org. Chem. 1997, 62, 3748.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 3748
-
-
Ye, D.1
Fringuelli, F.2
Piermatti, O.3
Pizzo, F.4
-
12
-
-
0033534352
-
-
de Sousa, S. E.; Kee, A.; O'Brien, P.; Watson, S. T. Tetrahedron Lett. 1999, 40, 387.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 387
-
-
De Sousa, S.E.1
Kee, A.2
O'Brien, P.3
Watson, S.T.4
-
13
-
-
0141975279
-
-
Donohoe, T. J.; Mitchell, L.; Waring, M. J.; Helliwell, M.; Bell, A.; Newcombe, N. J. Org. Biomol. Chem. 2003, 1, 2173.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 2173
-
-
Donohoe, T.J.1
Mitchell, L.2
Waring, M.J.3
Helliwell, M.4
Bell, A.5
Newcombe, N.J.6
-
14
-
-
53649111621
-
-
Aciro, C.; Claridge, T. D. W.; Davies, S. G.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Org. Biomol. Chem. 2008, 6, 3751.
-
(2008)
Org. Biomol. Chem.
, vol.6
, pp. 3751
-
-
Aciro, C.1
Claridge, T.D.W.2
Davies, S.G.3
Roberts, P.M.4
Russell, A.J.5
Thomson, J.E.6
-
15
-
-
53549104716
-
-
Aciro, C.; Davies, S. G.; Roberts, P. M.; Russell, A. J.; Smith, A. D.; Thomson, J. E. Org. Biomol. Chem. 2008, 6, 3762.
-
(2008)
Org. Biomol. Chem.
, vol.6
, pp. 3762
-
-
Aciro, C.1
Davies, S.G.2
Roberts, P.M.3
Russell, A.J.4
Smith, A.D.5
Thomson, J.E.6
-
16
-
-
36749051660
-
-
For selected recent examples, see
-
For selected recent examples, see: Cailleau, T.; Cooke, J. W. B.; Davies, S. G.; Ling, K. B.; Naylor, A.; Nicholson, R. L.; Price, P. D.; Roberts, P. M.; Russell, A. J.; Smith, A. D.; Thomson, J. E. Org. Biomol. Chem. 2007, 5, 3922.
-
(2007)
Org. Biomol. Chem.
, vol.5
, pp. 3922
-
-
Cailleau, T.1
Cooke, J.W.B.2
Davies, S.G.3
Ling, K.B.4
Naylor, A.5
Nicholson, R.L.6
Price, P.D.7
Roberts, P.M.8
Russell, A.J.9
Smith, A.D.10
Thomson, J.E.11
-
17
-
-
42349103981
-
-
Abraham, E.; Davies, S. G.; Millican, N. L.; Nicholson, R. L.; Roberts, P. M.; Smith, A. D. Org. Biomol. Chem. 2008, 6, 1655.
-
(2008)
Org. Biomol. Chem.
, vol.6
, pp. 1655
-
-
Abraham, E.1
Davies, S.G.2
Millican, N.L.3
Nicholson, R.L.4
Roberts, P.M.5
Smith, A.D.6
-
18
-
-
42349111665
-
-
Abraham, E.; Brock, E. A.; Candela-Lena, J. I.; Davies, S. G.; Georgiou, M.; Nicholson, R. L.; Perkins, J. H.; Roberts, P. M.; Russell, A. J.; Sánchez-Fernández, E. M.; Scott, P. M.; Smith, A. D.; Thomson, J. E. Org. Biomol. Chem. 2008, 6, 1665.
-
(2008)
Org. Biomol. Chem.
, vol.6
, pp. 1665
-
-
Abraham, E.1
Brock, E.A.2
Candela-Lena, J.I.3
Davies, S.G.4
Georgiou, M.5
Nicholson, R.L.6
Perkins, J.H.7
Roberts, P.M.8
Russell, A.J.9
Sánchez-Fernández, E.M.10
Scott, P.M.11
Smith, A.D.12
Thomson, J.E.13
-
19
-
-
59949088993
-
-
Davies, S. G.; Durbin, M. J.; Goddard, E. C.; Kelly, P. M.; Kurosawa, W.; Lee, J. A.; Nicholson, R. L.; Price, P. D.; Roberts, P. M.; Russell, A. J.; Scott, P. M.; Smith, A. D. Org. Biomol. Chem. 2009, 7, 761.
-
(2009)
Org. Biomol. Chem.
, vol.7
, pp. 761
-
-
Davies, S.G.1
Durbin, M.J.2
Goddard, E.C.3
Kelly, P.M.4
Kurosawa, W.5
Lee, J.A.6
Nicholson, R.L.7
Price, P.D.8
Roberts, P.M.9
Russell, A.J.10
Scott, P.M.11
Smith, A.D.12
-
20
-
-
64349101662
-
-
Aciro, C.; Davies, S. G.; Kurosawa, W.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Org. Lett. 2009, 11, 1333.
-
(2009)
Org. Lett.
, vol.11
, pp. 1333
-
-
Aciro, C.1
Davies, S.G.2
Kurosawa, W.3
Roberts, P.M.4
Russell, A.J.5
Thomson, J.E.6
-
22
-
-
0031911359
-
-
(a) For example, see
-
(a) For example, see: Iranpoor, N.; Shekarriz, M.; Shiriny, F. Synth. Commun. 1998, 28, 347.
-
(1998)
Synth. Commun.
, vol.28
, pp. 347
-
-
Iranpoor, N.1
Shekarriz, M.2
Shiriny, F.3
-
23
-
-
0036431512
-
-
(b) Yoo, D.-W.; Yoo, S.-K.; Kim, C.; Lee, J.-K. J. Chem. Soc., Dalton Trans. 2002, 3931.
-
(2002)
J. Chem. Soc., Dalton Trans.
, pp. 3931
-
-
Yoo, D.-W.1
Yoo, S.-K.2
Kim, C.3
Lee, J.-K.4
-
24
-
-
8444242244
-
-
(c) Iranpoor, N.; Firouzabadi, H.; Aghapour, G.; Nahid, A. Bull. Chem. Soc. Jpn. 2004, 77, 1885.
-
(2004)
Bull. Chem. Soc. Jpn.
, vol.77
, pp. 1885
-
-
Iranpoor, N.1
Firouzabadi, H.2
Aghapour, G.3
Nahid, A.4
-
25
-
-
44649169264
-
-
(d) Han, J. H.; Hong, S. J.; Lee, E. Y.; Lee, J. H.; Kim, H. J.; Kwak, H.; Kim, C. Bull. Korean Chem. Soc. 2005, 26, 1434.
-
(2005)
Bull. Korean Chem. Soc.
, vol.26
, pp. 1434
-
-
Han, J.H.1
Hong, S.J.2
Lee, E.Y.3
Lee, J.H.4
Kim, H.J.5
Kwak, H.6
Kim, C.7
-
31
-
-
37049112534
-
-
Baldwin, J. E.; Adlington, R. M.; Chondrogianni, J.; Edenborough, M. S.; Keeping, J. W.; Ziegler, C. B. J. Chem. Soc., Chem. Commun. 1985, 816.
-
(1985)
J. Chem. Soc., Chem. Commun.
, pp. 816
-
-
Baldwin, J.E.1
Adlington, R.M.2
Chondrogianni, J.3
Edenborough, M.S.4
Keeping, J.W.5
Ziegler, C.B.6
-
32
-
-
0346656525
-
-
O'Brien, P.; Childs, A. C.; Ensor, G. J.; Hill, C. L.; Kirby, J. P.; Dearden, M. J.; Oxenford, S. J.; Rosser, C. M. Org. Lett. 2003, 5, 4955.
-
(2003)
Org. Lett.
, vol.5
, pp. 4955
-
-
O'Brien, P.1
Childs, A.C.2
Ensor, G.J.3
Hill, C.L.4
Kirby, J.P.5
Dearden, M.J.6
Oxenford, S.J.7
Rosser, C.M.8
-
33
-
-
0037111592
-
-
Several instances of syn-selective osmylation and epoxidation reactions of 3-substituted cyclopentenes which proceed in the absence of any obvious associative interactions (e.g., hydrogen bonding) in the transition state have been reported; see: (a)
-
Several instances of syn-selective osmylation and epoxidation reactions of 3-substituted cyclopentenes which proceed in the absence of any obvious associative interactions (e.g., hydrogen bonding) in the transition state have been reported; see: (a) Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.; Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 7946
-
-
Donohoe, T.J.1
Blades, K.2
Moore, P.R.3
Waring, M.J.4
Winter, J.J.G.5
Helliwell, M.6
Newcombe, N.J.7
Stemp, G.8
-
36
-
-
0024802464
-
-
Poli has proposed a model to account for these observations, in which attack on the syn-face is favoured due to minimization of torsional strain in the transition state; see
-
Poli has proposed a model to account for these observations, in which attack on the syn-face is favoured due to minimization of torsional strain in the transition state; see: Poli, G. Tetrahedron Lett. 1989, 30, 7385.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 7385
-
-
Poli, G.1
-
37
-
-
33646463586
-
-
Houk has coined the term "torsional steering" for this effect; see
-
Houk has coined the term "torsional steering" for this effect; see: Cheong, P. H.-Y.; Yun, H.; Danishefsky, S. J.; Houk, K. N. Org. Lett. 2006, 8, 1513.
-
(2006)
Org. Lett.
, vol.8
, pp. 1513
-
-
Cheong, P.H.-Y.1
Yun, H.2
Danishefsky, S.J.3
Houk, K.N.4
-
40
-
-
69549144421
-
-
note
-
H 4.94 (dd, J 7.7, 4.2), 4.97-5.03 (m), 5.29 (dd, J 6.2, 2.9)]. Purification of the crude reaction mixture gave 22 in 83% yield and >99:1 dr, while transesterification of the crude reaction mixture gave an 89:11 mixture of 24:35.
-
-
-
-
41
-
-
69549152418
-
-
note
-
4 giving crystals of suitable quality for X-ray analysis.
-
-
-
-
42
-
-
0031911359
-
-
See ref 9d and
-
See ref 9d and: Iranpoor, N.; Shekarriz, M.; Shiriny, F. Synth. Commun. 1998, 28, 347.
-
(1998)
Synth. Commun.
, vol.28
, pp. 347
-
-
Iranpoor, N.1
Shekarriz, M.2
Shiriny, F.3
-
44
-
-
0000048225
-
-
Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 2428
-
-
Denmark, S.E.1
Barsanti, P.A.2
Wong, K.-T.3
Stavenger, R.A.4
-
45
-
-
1542532787
-
-
For a discussion of the conformation of cyclooctane derivatives such as cis-cyclooctene, see
-
For a discussion of the conformation of cyclooctane derivatives such as cis-cyclooctene, see: Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981.
-
(1981)
Tetrahedron
, vol.37
, pp. 3981
-
-
Still, W.C.1
Galynker, I.2
-
47
-
-
0000874930
-
-
Cope, A. C.; Keough, A. H.; Peterson, P. E.; Simmons, H. E.; Wood, G. W. J. Am. Chem. Soc. 1957, 79, 3900.
-
(1957)
J. Am. Chem. Soc.
, vol.79
, pp. 3900
-
-
Cope, A.C.1
Keough, A.H.2
Peterson, P.E.3
Simmons, H.E.4
Wood, G.W.5
-
49
-
-
0032489928
-
-
Leong, M. K.; Mastryukov, V. S.; Boggs, J. E. J. Mol. Struct. 1998, 445, 149.
-
(1998)
J. Mol. Struct.
, vol.445
, pp. 149
-
-
Leong, M.K.1
Mastryukov, V.S.2
Boggs, J.E.3
-
50
-
-
0008841387
-
-
Abraham, R. J.; Castellazzi, I.; Sancassan, F.; Smith, T. A. D. J. Chem. Soc., Perkin Trans. 2 1999, 99.
-
(1999)
J. Chem. Soc., Perkin Trans. 2
, pp. 99
-
-
Abraham, R.J.1
Castellazzi, I.2
Sancassan, F.3
Smith, T.A.D.4
-
51
-
-
57649180499
-
-
2- (followed by hydrolysis) may occur. For a very recent example, see
-
2- (followed by hydrolysis) may occur. For a very recent example, see: Cavdar, H.; Saracoglu, N. Tetrahedron 2009, 65, 985.
-
(2009)
Tetrahedron
, vol.65
, pp. 985
-
-
Cavdar, H.1
Saracoglu, N.2
-
52
-
-
0642293603
-
-
Winstein, S.; Hess, H. V.; Buckles, R. E. J. Am. Chem. Soc. 1942, 64, 2157.
-
(1942)
J. Am. Chem. Soc.
, vol.64
, pp. 2157
-
-
Winstein, S.1
Hess, H.V.2
Buckles, R.E.3
-
53
-
-
0038731550
-
-
Roberts, J. D.; Young, W. G.; Winstein, S. J. Am. Chem. Soc. 1942, 64, 2796.
-
(1942)
J. Am. Chem. Soc.
, vol.64
, pp. 2796
-
-
Roberts, J.D.1
Young, W.G.2
Winstein, S.3
-
54
-
-
69549145255
-
-
note
-
The regiochemistry within 36 and 37 was arbitrarily assigned.
-
-
-
-
55
-
-
69549099482
-
-
note
-
3). (Chemical Equation Presented)
-
-
-
-
56
-
-
69549147280
-
-
note
-
A range of Brønsted acids were screened for their ability to promote crystallization of 39 as the corresponding ammonium salt, with 2-methyl-5- nitrobenzenesulfonic acid giving crystals of suitable quality for X-ray analysis.
-
-
-
-
57
-
-
69549153941
-
-
note
-
The regiochemistry within 45 and 46 was arbitrarily assigned.
-
-
-
-
58
-
-
0001408683
-
-
Whitten, J. P.; McCarthy, J. R.; Whalon, M. R. J. Org. Chem. 1985, 50, 4399.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 4399
-
-
Whitten, J.P.1
McCarthy, J.R.2
Whalon, M.R.3
-
59
-
-
69549151509
-
-
note
-
2H gave 53 as the major product (>95%) along with trace amounts of unidentifiable species. Recrystallization of the crude reaction mixture gave 53 in 87% yield and >99:1 dr, while transesterification gave 54 in >95:5 dr.
-
-
-
-
60
-
-
69549142139
-
-
note
-
The regiochemistry within 56 and 57 was arbitrarily assigned.
-
-
-
-
61
-
-
69549132903
-
-
note
-
3). (Chemical Equation Presented)
-
-
-
-
64
-
-
0023813086
-
-
Borcherding, D. R.; Narayanan, S.; Hasobe, M.; McKee, J. G.; Keller, B. T.; Borchardt, R. T. J. Med. Chem. 1988, 31, 1729.
-
(1988)
J. Med. Chem.
, vol.31
, pp. 1729
-
-
Borcherding, D.R.1
Narayanan, S.2
Hasobe, M.3
McKee, J.G.4
Keller, B.T.5
Borchardt, R.T.6
-
65
-
-
69549098641
-
-
note
-
Direct formation of N,N-dibenzyl-protected amine 65 from bromide 63 via displacement with dibenzylamine was not as efficacious.
-
-
-
-
66
-
-
69549148874
-
-
note
-
1HNMR "titration experiment" as described for allylic amines 14-16.
-
-
-
-
68
-
-
0003294908
-
-
A "strong" hydrogen bond is observed between C(2)O-H. . .N, and a "weak" hydrogen bond is observed between C(1)O-H. . .O-C(2); see: Desiraju, G. R., Steiner, T., Eds.; Oxford University Press: Oxford
-
A "strong" hydrogen bond is observed between C(2)O-H. . .N, and a "weak" hydrogen bond is observed between C(1)O-H. . .O-C(2); see: Desiraju, G. R. The Weak Hydrogen Bond in Structural Chemistry and Biology; Desiraju, G. R., Steiner, T., Eds.; Oxford University Press: Oxford, 1999; p 13.
-
(1999)
The Weak Hydrogen Bond in Structural Chemistry and Biology
, pp. 13
-
-
Desiraju, G.R.1
-
69
-
-
69549148072
-
-
note
-
2,3 4.6); in addition, it is notable that both OH protons are observable, appearing as broad singlets at δH 2.55 and 6.75.
-
-
-
-
70
-
-
69549093882
-
-
note
-
The stereo- and regiochemistries within 77 and 78 were subsequently established by comparison with authentic samples prepared via ring-opening of syn- and anti-epoxides 79 and 80, respectively.
-
-
-
-
71
-
-
0000898113
-
-
Chini, M.; Crotti, P.; Flippin, L. A.; Gardelli, C.; Macchia, F. J. Org. Chem. 1992, 57, 1713.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 1713
-
-
Chini, M.1
Crotti, P.2
Flippin, L.A.3
Gardelli, C.4
Macchia, F.5
-
72
-
-
69549149935
-
-
note
-
Hydrogen-bonded delivery of the conjugate base to C(2) by the protonated N,N-dibenzylaminomethyl group may also be important in determining the regioselectivity of the ring-opening reaction.
-
-
-
-
73
-
-
69549142137
-
-
note
-
The regiochemistry within 86 and 87 was arbitrarily assigned.
-
-
-
-
74
-
-
69549153030
-
-
note
-
2, -78 °C, 2 h, then MeOH, HCl, rt, 24 h). (Chemical Equation Presented)
-
-
-
-
75
-
-
69549152417
-
-
note
-
The regiochemistry within 90 and 91 was arbitrarily assigned.
-
-
-
-
76
-
-
69549094734
-
-
Chemical Crystallography Laboratory, University of Oxford, UK
-
Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, C. K.; Watkin, D. J. CRYSTALS 2001, issue 11, Chemical Crystallography Laboratory, University of Oxford, UK.
-
(2001)
CRYSTALS
, Issue.11
-
-
Betteridge, P.W.1
Carruthers, J.R.2
Cooper, R.I.3
Prout, C.K.4
Watkin, D.J.5
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