Prolinol

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Prolinol
D-Prolinol.svg L-Prolinol.svg
Identifiers
CAS number 68832-13-3 YesY
(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 (187 °F; 359 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.

Preparation[edit]

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.

Use[edit]

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]

See also[edit]

References[edit]

  1. ^ 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).
  2. ^ Enders D.; Fey P.; Kipphardt, H. [1] Organic Syntheses, Collected Volume 8, p.26 (1993).
  3. ^ Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1. 
  4. ^ 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.