Prolinol
From Wikipedia, the free encyclopedia
| Prolinol | |
|---|---|
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(R or S) 2-pyrrolidinemethanol |
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| Identifiers | |
| CAS number | 68832-13-3  , (D-prolinol) [23356-96-9] (L-prolinol) |
| Properties | |
| Molecular formula | C5H11NO |
| Molar mass | 101.15 g/mol |
| Appearance | Liquid |
| Density | 1.036 g/mL liquid |
| Boiling point |
74-76 °C at 2 mmHg |
| Hazards | |
| R-phrases | 36/37/38 |
| S-phrases | 26-36 |
| Main hazards | Irritant |
| Flash point | 86 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms.
Contents |
[edit] Preparation
Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.[1][2] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.
[edit] Use
Prolinol is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or chiral auxiliary reagent in the Hajos-Parrish-Eder-Sauer-Wiechert reaction, the Baylis-Hillman reaction, Noyori type reaction and the Michael reaction. [3][4]
[edit] See also
[edit] References
- ^ Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Reduction of α-Amino Acids: L-Valinol Organic Syntheses, Collected Volume 7, p.530 (1990).
- ^ Enders D.; Fey P.; Kipphardt, H. [1] Organic Syntheses, Collected Volume 8, p.26 (1993).
- ^ Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1.
- ^ Shinichi Itsuno, Koichi Ito, Akira Hirao and Seiichi Nakahama (1984). "Asymmetric synthesis using chirally modified borohydrides. Part 2. Enantioselective reduction of ketones with polymeric (S)-prolinol–borane reagent". J. Chem. Soc., Perkin Trans. 1 (12): 2887–2895. doi:10.1039/P19840002887.
