The mechanism of epoxidation of chiral allyl amines has been investigated. The intrinsic stereoselectivity for epoxidation is shown to be approximately 5:1 and is independent of the nitrogen substituent. However, the nature of the N-protecting group influences the stability of the undesired epoxide to the acidic media, with the minor diastereomer undergoing preferential decomposition. Conditions are reported for the highly stereoselective synthesis of epoxide 9R, an important building block in the synthesis of several enzyme inhibitors.
STEREOSELECTIVE SYNTHESIS OF PROTECTED AMINO ALKYL EPOXIDES / S. ROMEO, D. RICH. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 35:28(1994), pp. 4939-4942.
STEREOSELECTIVE SYNTHESIS OF PROTECTED AMINO ALKYL EPOXIDES
S. ROMEOPrimo
;
1994
Abstract
The mechanism of epoxidation of chiral allyl amines has been investigated. The intrinsic stereoselectivity for epoxidation is shown to be approximately 5:1 and is independent of the nitrogen substituent. However, the nature of the N-protecting group influences the stability of the undesired epoxide to the acidic media, with the minor diastereomer undergoing preferential decomposition. Conditions are reported for the highly stereoselective synthesis of epoxide 9R, an important building block in the synthesis of several enzyme inhibitors.
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
