L-Proline

• Catalog No.: A10199
• CAS Number: 147-85-3
• M. F.: C5H9NO2
• M. W.: 115.13046
• Purity: 99%

SYNONYMS

• Title: L-脯氨酸
• IUPAC name: (2S)-pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: L-proline
• Synonyms: (S)-Pyrrolidine-2-carboxylic acid; H-Pro-OH

DATABASE IDS

• MDL Number: MFCD00064318
• CAS Number: 147-85-3
• Beilstein Number: 80810
• Merck Index: 147780
• EC Number: 205-702-2

PROPERTIES

• Purity: 99%
• Density: 1.36
• Melting Point: ca 225°C dec.
• Optical Rotation: -84 (c=1 in water)
• RTECS: TW3584000
• Storage Warning: Hygroscopic
• TSCA Listed: 是

REFERENCES

• For use as a catalyst in an asymmetric aldol cyclization, see: Org. Synth. Coll., 7, 363 (1990). For reaction scheme, see 2-Methylcyclopentane-1,3-dione, A13936. For use in a direct enantioselective crossed aldol reaction with aldehydes, see: J. Am. Chem. Soc., 124, 6798 (2002). For use as an organoctalyst in direct aldol reactions of ɑ-oxyaldehydes, as the first step in a two-step synthesis of carbohydrates, see: Angew. Chem. Int. Ed., 43, 2152 (2004). Mediates the enantioselective borane reduction of ketones to chiral alcohols with moderate to good ee: Monatsh. Chem., 131, 91 (2000). Also used to induce high ee in the ɑ-amination of aldehydes with Dibenzyl azodicarboxylate, L19347: J. Am. Chem. Soc., 124, 5656 (2002), or Diethyl azodicarboxylate, L19348: Angew. Chem. Int. Ed., 41, 1790 (2002).
• For a review of the use of proline as a chiral catalyst, see: Synlett, 1675 (2001); Synlett, 1973 (2006).
• For preparation from L-proline of the chiral hydrazone "SAMP", and enantioselective syntheses using the RAMP/ SAMP methodology, see: Org. Synth. Coll., 8, 26, 403 (1985).
• For formation of a fused pyrrolidino-oxazolidinone, and use of the product in a synthesis of enantiopure ɑ-branched amino acids, see: Org. Synth. Coll., 9, 626 (1998); for reaction scheme, see Trimethylacetaldehyde, A15013.
• The Li salt has been used as a catalyst for the Michael addition of dimethyl malonate to ɑ?-unsaturated aldehydes: J. Chem. Soc., Chem. Commun., 1088 (1991).