(4S)-(-)-Isopropyl-2-oxazolidinone

• Catalog No.: A14029
• CAS Number: 17016-83-0
• M. F.: C6H11NO2
• M. W.: 129.15704
• Purity: 98%

SYNONYMS

• Title: (4S)-(-)-异丙基-2-恶唑啉酮
• IUPAC name: (4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-isopropyl-1,3-oxazolidin-2-one

DATABASE IDS

• Beilstein Number: 3588198
• CAS Number: 17016-83-0
• MDL Number: MFCD00010847

PROPERTIES

• Purity: 98%
• Melting Point: 70-74°C
• Optical Rotation: -17 (c=6 in ethanol)
• TSCA Listed: 否

REFERENCES

• Alkyl carboxamides derived from the N-acylation of the oxazolidinone form enolates which undergo highly enantioselective aldol condensation with aldehydes. The products readily undergo hydrolysis, e.g. with base, to give chiral ? -hydroxyacids, with consequent easy recovery and recycle of the chiral auxiliary: J. Am. Chem. Soc., 103, 2127 (1981); Tetrahedron, 27, 897 (1986); Tetrahedron Lett., 31, 4699 (1990); J. Org. Chem., 56, 2489 (1991). For reaction scheme, see (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.
• The enolates of the N-acyloxazolidinones can also undergo a variety of other enantioselective reactions including alkylation: J. Am. Chem. Soc., 104, 1737 (1982); acylation: J. Am. Chem. Soc., 106, 1154 (1984):
  
• Bromination (NBS), followed by azide displacement, gives a route to chiral amino acids: Tetrahedron Lett ., 28, 1123 (1987). Direct electrophilic azidation with triisopropylbenzenesulfonyl azide has also been used to effect this transformation: J. Am. Chem. Soc., 112, 4011 (1990).
• Chiral auxiliary introduced by Evans for use in enantioselective reactions.
• See also (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.