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2542446198
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4744346531
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36148970785
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21
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77955352647
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22
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17444396764
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23
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77955402345
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ξ-Hydroxy-α,β-unsaturated ester 13 was prepared in 55% yield [96:4 E/Z ratio] via the one-pot treatment of δ-valerolactone with DIBAL-H, tert-butyl 2-(diethoxy-phosphoryl)acetate and BuLi at-78 °C. See ref. 9 for details
-
ξ-Hydroxy-α,β-unsaturated ester 13 was prepared in 55% yield [96:4 E/Z ratio] via the one-pot treatment of δ-valerolactone with DIBAL-H, tert-butyl 2-(diethoxy-phosphoryl)acetate and BuLi at-78 °C. See ref. 9 for details.
-
-
-
-
27
-
-
33751499135
-
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Holmes, A. B.; Smith, A. L.; Williams, S. F. J. Org. Chem. 1991, 56, 1393.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 1393
-
-
Holmes, A.B.1
Smith, A.L.2
Williams, S.F.3
-
28
-
-
77955379788
-
-
For a related example, see ref. 11a
-
For a related example, see ref. 11a.
-
-
-
-
29
-
-
37049072079
-
-
β-Amino aldehydes are known to be unstable with respect to retro-Michael reactions; see
-
β-Amino aldehydes are known to be unstable with respect to retro-Michael reactions; see: Carruthers, W.; Moses, R. C. J. Chem. Soc., Perkin Trans. 1 1988, 2251.
-
(1988)
J. Chem. Soc., Perkin Trans.
, vol.1
, pp. 2251
-
-
Carruthers, W.1
Moses, R.C.2
-
30
-
-
77955343389
-
-
B]
-
B].
-
-
-
-
32
-
-
77955346854
-
-
+: 126.1283; found: 126.1278
-
+: 126.1283; found: 126.1278.
-
-
-
-
33
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0035945769
-
-
Yamazaki, N.; Dokoshi, W.; Kibayashi, C. Org Lett. 2001, 3, 193.
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-
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Yamazaki, N.1
Dokoshi, W.2
Kibayashi, C.3
-
34
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0028953345
-
-
Within this area, Monterrey et al. have shown that alkylation of N-Cbz protected piperidin-2-yl-acetates with ethyl bromoacetate can lead to successful ring closure by removal of the N-Cbz protecting group in a tandem hydrogenolysis-hydrogenation step to give the corresponding hexahydro-indolizin- 3-one; see
-
Within this area, Monterrey et al. have shown that alkylation of N-Cbz protected piperidin-2-yl-acetates with ethyl bromoacetate can lead to successful ring closure by removal of the N-Cbz protecting group in a tandem hydrogenolysis-hydrogenation step to give the corresponding hexahydro-indolizin- 3-one; see: Monterrey, I. M. G.; González-Muñiz, R.; Herranz, R.; Garcia-López, M. T. Tetrahedron 1995, 51, 2729.
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(1995)
Tetrahedron
, vol.51
, pp. 2729
-
-
Monterrey, I.M.G.1
González-Muñiz, R.2
Herranz, R.3
Garcia-López, M.T.4
-
35
-
-
37049071174
-
-
The anti-configuration of the alkylation was assigned on the basis of the established preferential anti-alkylations of lithium β-amino enolates, see
-
The anti-configuration of the alkylation was assigned on the basis of the established preferential anti-alkylations of lithium β-amino enolates, see: (a) Davies, S. G.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129.
-
(1994)
J. Chem. Soc., Perkin Trans.
, vol.1
, pp. 1129
-
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Davies, S.G.1
Walters, I.A.S.2
-
36
-
-
0033579646
-
-
(b) Ledoux, S.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 1999, 40, 9019.
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(1999)
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, vol.40
, pp. 9019
-
-
Ledoux, S.1
Célérier, J.-P.2
Lhommet, G.3
-
37
-
-
77955405957
-
-
+
-
+.
-
-
-
-
38
-
-
0025344784
-
-
Both diastereomers of l-(hydroxymethyl)octahydro-indolizidine (40) have previously been reported, see
-
Both diastereomers of l-(hydroxymethyl)octahydro-indolizidine (40) have previously been reported, see: (a) Nagao, Y.; Dai, W.; Ochiai, M.; Tsukagoshi, S.; Fujitalc, E. J. Org. Chem. 1990, 55, 1148.
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(1990)
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, vol.55
, pp. 1148
-
-
Nagao, Y.1
Dai, W.2
Ochiai, M.3
Tsukagoshi, S.4
Fujitalc, E.5
-
39
-
-
2742538971
-
-
(b) Pandey, G.; Lakshmaiah, G.; Gadre, S. M. Indian J. Chem., Sect. B: Org. Chem. Inch Med. Chem. 1996, 35, 91.
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, vol.35
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-
-
Pandey, G.1
Lakshmaiah, G.2
Gadre, S.M.3
-
41
-
-
77955412067
-
-
Some discrepancies exist between the reported characterisation data for 40 and its epimer; these will be highlighted in a forthcoming publication from this laboratory. However, our synthesis unambiguously confirms the relative and absolute configuration of 40
-
Some discrepancies exist between the reported characterisation data for 40 and its epimer; these will be highlighted in a forthcoming publication from this laboratory. However, our synthesis unambiguously confirms the relative and absolute configuration of 40.
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