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(4S)-(-)-Isopropyl-2-oxazolidinone, 98% - CAS 17016-83-0 - Formula C6H11NO2


Certificate of Analysis

(4S)-(-)-Isopropyl-2-oxazolidinone, 98%

CAS: 17016-83-0 MDL: MFCD00010847  
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Chemical Properties

Formula: C6H11NO2  Melting point: 70-74°
Formula weight: 129.16  Optical Rotation: -17° (c=6 in ethanol)

Literature References

Chiral auxiliary introduced by Evans for use in enantioselective reactions.

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 ß -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).

See also (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.

Other References

Beilstein: 3588198
Harmonized Tariff Code:   2934.99

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