In:
Synthesis, Georg Thieme Verlag KG, Vol. 52, No. 07 ( 2020-04), p. 1047-1059
Abstract:
An asymmetric phase-transfer-catalyzed N-alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.
Type of Medium:
Online Resource
ISSN:
0039-7881
,
1437-210X
DOI:
10.1055/s-0039-1690751
Language:
English
Publisher:
Georg Thieme Verlag KG
Publication Date:
2020
detail.hit.zdb_id:
204080-3
detail.hit.zdb_id:
2033062-5
