-
2
-
-
0002667764
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-
Reviews of the Mitsunobu reaction: (a) Mitsunobu, O. Synthesis 1981, 1; (b) Hughes, D. L. Org. Reactions 1992, 42, 335; (c) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
-
(1981)
Synthesis
, pp. 1
-
-
Mitsunobu, O.1
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3
-
-
0000414496
-
-
Reviews of the Mitsunobu reaction: (a) Mitsunobu, O. Synthesis 1981, 1; (b) Hughes, D. L. Org. Reactions 1992, 42, 335; (c) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
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(1992)
Org. Reactions
, vol.42
, pp. 335
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-
Hughes, D.L.1
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4
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-
0001640928
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-
Reviews of the Mitsunobu reaction: (a) Mitsunobu, O. Synthesis 1981, 1; (b) Hughes, D. L. Org. Reactions 1992, 42, 335; (c) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
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(1996)
Org. Prep. Proc. Int.
, vol.28
, pp. 127
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-
Hughes, D.L.1
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6
-
-
0001611415
-
-
For intermolecular reactions: (a) Bittner, S.; Assaf, Y. Chem. Ind. (London) 1975, 281; (b) Subramanian, R. S.; Balasubramanian, K. K. Synth. Commun. 1989, 19, 1255; (c) Subramanian, R. S.; Balasubramanian, K. K. Tetrahedron Lett. 1989, 30, 2297; (d) Brunner, H.; Hankofer, P.; Treittinger, B. Chem. Ber. 1990, 1029. For intramolecular reactions: (d) Reisch, J.; Voerste, A. A. W. J. Chem. Soc., Perkin Trans. 1 1994, 3251.
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(1975)
Chem. Ind. (London)
, pp. 281
-
-
Bittner, S.1
Assaf, Y.2
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7
-
-
84972996329
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-
For intermolecular reactions: (a) Bittner, S.; Assaf, Y. Chem. Ind. (London) 1975, 281; (b) Subramanian, R. S.; Balasubramanian, K. K. Synth. Commun. 1989, 19, 1255; (c) Subramanian, R. S.; Balasubramanian, K. K. Tetrahedron Lett. 1989, 30, 2297; (d) Brunner, H.; Hankofer, P.; Treittinger, B. Chem. Ber. 1990, 1029. For intramolecular reactions: (d) Reisch, J.; Voerste, A. A. W. J. Chem. Soc., Perkin Trans. 1 1994, 3251.
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(1989)
Synth. Commun.
, vol.19
, pp. 1255
-
-
Subramanian, R.S.1
Balasubramanian, K.K.2
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8
-
-
0024511841
-
-
For intermolecular reactions: (a) Bittner, S.; Assaf, Y. Chem. Ind. (London) 1975, 281; (b) Subramanian, R. S.; Balasubramanian, K. K. Synth. Commun. 1989, 19, 1255; (c) Subramanian, R. S.; Balasubramanian, K. K. Tetrahedron Lett. 1989, 30, 2297; (d) Brunner, H.; Hankofer, P.; Treittinger, B. Chem. Ber. 1990, 1029. For intramolecular reactions: (d) Reisch, J.; Voerste, A. A. W. J. Chem. Soc., Perkin Trans. 1 1994, 3251.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 2297
-
-
Subramanian, R.S.1
Balasubramanian, K.K.2
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9
-
-
0004217504
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-
For intermolecular reactions: (a) Bittner, S.; Assaf, Y. Chem. Ind. (London) 1975, 281; (b) Subramanian, R. S.; Balasubramanian, K. K. Synth. Commun. 1989, 19, 1255; (c) Subramanian, R. S.; Balasubramanian, K. K. Tetrahedron Lett. 1989, 30, 2297; (d) Brunner, H.; Hankofer, P.; Treittinger, B. Chem. Ber. 1990, 1029. For intramolecular reactions: (d) Reisch, J.; Voerste, A. A. W. J. Chem. Soc., Perkin Trans. 1 1994, 3251.
-
(1990)
Chem. Ber.
, pp. 1029
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-
Brunner, H.1
Hankofer, P.2
Treittinger, B.3
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10
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-
37049069950
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-
For intermolecular reactions: (a) Bittner, S.; Assaf, Y. Chem. Ind. (London) 1975, 281; (b) Subramanian, R. S.; Balasubramanian, K. K. Synth. Commun. 1989, 19, 1255; (c) Subramanian, R. S.; Balasubramanian, K. K. Tetrahedron Lett. 1989, 30, 2297; (d) Brunner, H.; Hankofer, P.; Treittinger, B. Chem. Ber. 1990, 1029. For intramolecular reactions: (d) Reisch, J.; Voerste, A. A. W. J. Chem. Soc., Perkin Trans. 1 1994, 3251.
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(1994)
J. Chem. Soc., Perkin Trans. 1
, pp. 3251
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-
Reisch, J.1
Voerste, A.A.W.2
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11
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0034334748
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-
and references cited therein
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2/pyridine, Müller, P.; Rossier, J.-C. J. Chem. Soc., Perkin Trans. 2 2000, 2232 and references cited therein; (b) DAST, Wachtmeister, J.; Mühlman, A.; Classon, B.; Samuelsson, B. Tetrahedron 1999, 55, 10761 and references cited therein.
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(2000)
J. Chem. Soc., Perkin Trans. 2
, pp. 2232
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-
Müller, P.1
Rossier, J.-C.2
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12
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-
0033609762
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-
and references cited therein
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2/pyridine, Müller, P.; Rossier, J.-C. J. Chem. Soc., Perkin Trans. 2 2000, 2232 and references cited therein; (b) DAST, Wachtmeister, J.; Mühlman, A.; Classon, B.; Samuelsson, B. Tetrahedron 1999, 55, 10761 and references cited therein.
-
(1999)
Tetrahedron
, vol.55
, pp. 10761
-
-
Wachtmeister, J.1
Mühlman, A.2
Classon, B.3
Samuelsson, B.4
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13
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-
85031206183
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-
(±)-1 was made from alkylation of 4-(benzyloxy)phenol with methyl 2-bromobutyrate followed by α-methylation with methyl iodide and subsequent chiral HPLC separation afforded enantiomerically pure
-
Racemic ether (±)-1 was made from alkylation of 4-(benzyloxy)phenol with methyl 2-bromobutyrate followed by α-methylation with methyl iodide and subsequent chiral HPLC separation afforded enantiomerically pure (R)-1 and (S)-1 (communication with Dr. R. Desai in our laboratories).
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-
-
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14
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0032492980
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-
Attempts to synthesis chiral ether (S)-1 using the Pd-catalyzed cross-coupling of chiral alcohol (S)-2 and 4-(benzyloxy)phenyl bromide were unsuccessful. However, the copper-promoted cross-coupling of (S)-2 with 4-(benzyloxy)phenylboronic acid has afforded a low yield of (S)-1 with compete retention of configuration that was confirmed by chiral HPLC assay (unpublished results of Conlon, D. A.; Drahus, A. L. and Shi, Y.-J. in our laboratories). For the copper-promoted arylation of phenols with arylboronic acid, see: Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2937
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-
Evans, D.A.1
Katz, J.L.2
West, T.R.3
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15
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-
33947481591
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-
The chiral alcohol. and references cited therein
-
The chiral alcohol (S)-2 is activated by the α-ester moiety, see: Bordwell F.G., Brannen W.T. Jr. J. Am. Chem. Soc. 5:1964;4645. and references cited therein.
-
(1964)
J. Am. Chem. Soc.
, vol.5
, pp. 4645
-
-
Bordwell, F.G.1
Brannen W.T., Jr.2
-
16
-
-
18644383018
-
-
For synthesis of chiral alcohol
-
For synthesis of chiral alcohol (S)-2, see: Tan L., Chen C.-y., Frey L., King A.O., Tillyer R.D., Xu F., Zhao D., Grabowski E.J.J., Reider P.J., O'Shea P., Dagneau P., Wang X. Tetrahedron. 58:2002;7403.
-
(2002)
Tetrahedron
, vol.58
, pp. 7403
-
-
Tan, L.1
Chen, C.-y.2
Frey, L.3
King, A.O.4
Tillyer, R.D.5
Xu, F.6
Zhao, D.7
Grabowski, E.J.J.8
Reider, P.J.9
O'Shea, P.10
Dagneau, P.11
Wang, X.12
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17
-
-
85031199772
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-
For temperature effects on the Mitsunobu reaction, see Ref. 2b
-
For temperature effects on the Mitsunobu reaction, see Ref. 2b.
-
-
-
-
18
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-
85031195863
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-
The order of addition of reagents was critical, see Ref. 2b.
-
The order of addition of reagents was critical, see Ref. 2b.
-
-
-
-
19
-
-
85031208565
-
-
(S)-2 (0.76 g, 5.76 mmol) and DIAD (1.40 ml, 7.12 mmol) was made in toluene (4.0 ml) and then slowly added to a mixture of phenol
-
4), eluent (B): MeCN, gradient (25°C): A/B from 40/60 to 20/80 over 20 min, 1.0 ml/min, 210 nm, retention time: 9.84 min for (R)-1 and 13.38 min for (S)-1 ].
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-
-
-
20
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-
85031208802
-
-
13C) and LCMS.
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13C) and LCMS.
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