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Benzyl isocyanate, is used as a protected ammonia equivalent in the stereo selective ring-opening of chiral 2,3-epoxy alcohols (from Sharpless asymmetric epoxidation). The key step in the sequence involves intramolecular cyclization of the carbamate intermediate. It is also used in a multicomponent, stereospecific synthesis of 1,3-oxazinane-2,4-diones employing an Al-salph complex.
LL Ferstandig.; RA Scherrer. Mechanism of Isocyanate Reactions with Ethanol1. J. Am. Chem. Soc. 195981(18) , 4838-4842.
DG Hoare.; DE Koshland Jr. A procedure for the selective modification of carboxyl groups in proteins. J. Am. Chem. Soc. 196688(9) , 2057-2058.
Protected ammonia equivalent in the stereoselective ring-opening of chiral 2,3-epoxy alcohols (from Sharpless asymmetric epoxidation). The key step in the sequence involves intramolecular cyclization of the carbamate intermediate: J. Org. Chem., 50, 3752 (1985):
For general reactions of isocyanates, see Appendix 3.
Gefahrenhinweise (EU): H226-H301-H330-H315-H319-H334-H335
Flammable liquid and vapour. Toxic if swallowed. Fatal if inhaled. Causes skin irritation. Causes serious eye irritation. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause respiratory irritation.
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