In:
Angewandte Chemie International Edition, Wiley, Vol. 58, No. 8 ( 2019-02-18), p. 2418-2422
Abstract:
Both E ‐ and Z ‐ N ′‐alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure α‐amino acids. Generation of their enolate derivatives in the presence of K + and [18]crown‐6 induces intramolecular migration of the alkenyl group from N′ to Cα with retention of double bond geometry. DFT calculations indicate a partially concerted substitution mechanism. Hydrolysis of the enantiopure products under acid conditions reveals quaternary α‐alkenyl amino acids with stereodivergent control of both absolute configuration and double bond geometry.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.201813984
Language:
English
Publisher:
Wiley
Publication Date:
2019
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7