In:
Advanced Synthesis & Catalysis, Wiley, Vol. 351, No. 9 ( 2009-06), p. 1355-1362
Abstract:
magnified image A new class of primary amine‐thioureas based on tert ‐butyl esters of ( S )‐α‐amino acids and (1 S ,2 S )‐diphenylethylenediamine was synthesized and their activity as catalysts in Michael additions was evaluated. Derivatives based on di‐ tert ‐butyl aspartate and tert ‐butyl O ‐ tert ‐butyl threoninate provided the product of the reaction between trans‐ β‐nitrostyrene and acetone in quantitative yield and high enantioselectivity (87–91% ee ). All the thioureas based on tert ‐butyl esters of amino acids catalyzed the reaction of nitroolefins with acetophenone with high enantioselectivity (92–98% ee ). Thus, low‐cost, commercially available tert ‐butyl esters of natural amino acids are very important chiral building blocks for the construction of novel chiral thioureas able to catalyze asymmetric Michael additions with high enantioselectivity.
Type of Medium:
Online Resource
ISSN:
1615-4150
,
1615-4169
DOI:
10.1002/adsc.200800812
Language:
English
Publisher:
Wiley
Publication Date:
2009
detail.hit.zdb_id:
2041384-1
detail.hit.zdb_id:
2033084-4
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