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L-(+)-Valinol reacts with aldehydes and nitriles to form imines and oxazolines, respectively, for asymmetric synthesis. It is also used for preparation of 4-isopropyloxazolidinones, employed in stereocontrolled aldol and alkylation reactions, synthesis of chiral 2-thiazolidinethiones for aldol reactions, asymmetric alkylation of condensation product with keto acids, asymmetric reactions of its amidines and imines and oxidation of N-protected derivative to the aldehyde.
Y. Turgut.; H. Hoşgoren. Synthesis of chiral monoaza-15-crown-5 ethers from l-valinol and the enantiomeric recognition of chiral amines and their perchlorates salts. Tetrahedron: Asymmetry: Asymmetry. 2003, 14 (23), 3815-3818.
Hongge Jia.; Masahiro Teraguchi.; Toshiki Aoki.; Yunosuke Abe.; Takashi Kaneko.; Shingo Hadano.; Takeshi Namikoshi.; Edy Marwanta. Two Modes of Asymmetric Polymerization of Phenylacetylene Having a l-Valinol Residue and Two Hydroxy Groups. Macromolecules. 2009, 42 (1), 17-19.
Chiral auxiliary and building block. See also (4S)-(-)-Isopropyl-2-oxazolidinone, A14029 for derived reagents.
Hazard Statements: H315-H319
Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P280a-P264-P305+P351+P338-P321-P332+P313-P337+P313
Wear protective gloves and eye/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists: