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1-Methoxy-2-methyl-1-(trimethylsiloxy)propene is used in the synthesis of chiral β-lactams by reacting with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride. It acts as a catalyst or initiator in the group-transfer polymerization. It is also used as a versatile reagent in conjugate addition4 and aldol reactions.
Masahiro Yamanaka; Junji Itoh, Kohei Fuchibe; Takahiko Akiyama. Chiral Brønsted acid catalyzed enantioselective Mannich-type reaction.Journal of the American Chemical Society.2007,129 (21), 6756-6764..
Silyl ketene acetal. The silyl enol ether of methyl isobutyrate. Catalyst for the initiation of group transfer polymerization, for controlled polymerization of ɑß-unsaturated esters, ketones, nitriles and amides, in which the ketene acetal function is transferred along the growing polymer chain: J. Am. Chem. Soc., 105, 5706 (1983); Science, 222, 39 (1983).
In the presence of a Lewis acid e.g. TiCl4 or TMS-OTf, undergoes the Mukaiyama aldol reaction with aldehydes to give methyl ɑɑ-dimethyl-ß-hydroxy esters: Chem. Lett., 989 (1975); Synth. Commun., 13, 449 (1983). Excellent results are obtained in these reactions with lanthanide triflates, e.g. Yb(OTf)3, as catalysts: Synthesis, 371 (1993).
With imines, gives ß-amino esters or ß-lactams according to conditions: Tetrahedron Lett., 3643 (1977); Chem. Lett., 1397 (1989); Tetrahedron, 44, 4157 (1988).
Michael additions to enones, catalyzed by Yb(OTf)3, have also been reported: Tetrahedron Lett., 33, 6815 (1992).
Hazard Statements: H226-H315-H319-H335
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant