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EINECS Number: 203-485-9
Specific Gravity: 1.201
Flashpoint: 31°C (88°F)
HMIS Key: 3-3-2-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.4460
Application: Review of synthetic utility.1
Effects asymmetric allylation of aldehydes after reaction with chiral diols.2
Used in the highly enantioselective allylation of aromatic aldehydes.3,4
Enantioselectively allylates aryl aldehydes with high ee values.5
Undergoes enantioselective allylation of aldehydes to form homoallylic alcohols.6
Allylates carbonyls with base catalysis as opposed to allyltrimethylsilane (SIA0555.0), which requires Lewis acid catalysis.7
Chiral Phosphoramides catalyze the enantioselective allylation of aromatic, heteroaromatic, as well as cinnamyl aldehydes.8
Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 10-14.
2. Wang, Z. et al. J. Chem. Soc., Chem. Commun. 1996, 2261.
3. Shimada. T. et al. Org. Lett. 2002, 4, 2799.
4. Malkov, A. et al. Org. Lett. 2002, 4, 1047.
5. Simonini, V. et al. Adv. Synth. Catal. 2008, 350, 561.
6. Massa, A. et al. Tetrahedron: Asymmetry 2009, 20, 202.
7. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1993, 34, 3453.
8. Denmark, S. E. et al. J. Org. Chem. 1994, 59, 6161.
Additional Properties: ?Hvap: 9.4 kcal/mole