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2 (1 equiv) prior to addition of 4-fluoro-3-nitrobenzaldehyde (1 equiv, -80°C, 48 h, THF) which provided a more favorable 5:1 ratio of separable alcohol diastereomers (53% + 10%). Compound 14 has also been prepared by a threonine aldolase catalyzed aldol reaction: Vassilev, V.-P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 4081. We thank Wilna J. Moree and Professor C.-H. Wong for providing substantial quantities of 14.
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(1985)
Synthesis
, pp. 55
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-
Schöllkopf, U.1
Nozulak, J.2
Grauert, M.3
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116
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0029011504
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2 (1 equiv) prior to addition of 4-fluoro-3-nitrobenzaldehyde (1 equiv, -80°C, 48 h, THF) which provided a more favorable 5:1 ratio of separable alcohol diastereomers (53% + 10%). Compound 14 has also been prepared by a threonine aldolase catalyzed aldol reaction: Vassilev, V.-P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 4081. We thank Wilna J. Moree and Professor C.-H. Wong for providing substantial quantities of 14.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 4081
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-
Vassilev, V.-P.1
Uchiyama, T.2
Kajimoto, T.3
Wong, C.-H.4
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117
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8544264379
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note
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32 To date we have not been successful in enriching the optical purity of 17 by recrystallization as it has only been isolated as a foam.
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-
-
-
118
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8544241553
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Full experimental details are provided in the Supporting Information
-
Full experimental details are provided in the Supporting Information.
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-
-
-
119
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8544261982
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-
note
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3 wash rather than direct Chromatographic purification, additional undesired and unidentified reaction products were isolated.
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-
-
-
120
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8544245475
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note
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11ClSi requires 932.1957).
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-
-
-
121
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0024278363
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Badet, B.; Vermoote, P.; Le Goffic, F. Biochemistry 1988, 27, 2282. For the dehydration procedure: Liberek, B.; Buczel, Cz.; Grzunka, Z. Tetrahedron 1966, 22, 2303; Ressler, C.; Ratzkin, H. J. Org. Chem. 1961, 26, 3356.
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(1988)
Biochemistry
, vol.27
, pp. 2282
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Badet, B.1
Vermoote, P.2
Le Goffic, F.3
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122
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8544265828
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Badet, B.; Vermoote, P.; Le Goffic, F. Biochemistry 1988, 27, 2282. For
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(1966)
Tetrahedron
, vol.22
, pp. 2303
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Liberek, B.1
Buczel, Cz.2
Grzunka, Z.3
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123
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0002884465
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Badet, B.; Vermoote, P.; Le Goffic, F. Biochemistry 1988, 27, 2282. For the dehydration procedure: Liberek, B.; Buczel, Cz.; Grzunka, Z. Tetrahedron 1966, 22, 2303; Ressler, C.; Ratzkin, H. J. Org. Chem. 1961, 26, 3356.
-
(1961)
J. Org. Chem.
, vol.26
, pp. 3356
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-
Ressler, C.1
Ratzkin, H.2
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124
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8544239923
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note
-
Both the β-cyano-L-alanine methyl ester (79) and the pentafluorophenyl ester 80 were enantiomerically and diastereomerically purer going into the reaction.
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-
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