Substance
ID:716761
Names and Identifiers
IUPAC name
(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one
IUPAC Traditional name
(4S)-4-isopropyl-1,3-oxazolidin-2-one
Synonyms
(4S)-(-)-Isopropyl-2-oxazolidinone(4S)-(-)-异丙基-2-恶唑啉酮
Properties
Product Information
Purity
98%
Physical Property
Optical Rotation
-17 (c=6 in ethanol)
Melting Point
70-74°C
Safety Information
TSCA Listed
否
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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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):
• Chiral auxiliary introduced by Evans for use in enantioselective reactions.
• 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).
• See also (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.