4397-13-1Relevant articles and documents
Salalens and Salans Derived from 3-Aminopyrrolidine: Aluminium Complexation and Lactide Polymerisation
Britton, Luke,Ditz, Daniel,Beament, James,McKeown, Paul,Quilter, Helena C.,Riley, Kerry,Mahon, Mary F.,Jones, Matthew D.
, p. 2768 - 2773 (2019)
In this paper a series of 7 salalen ligands based on an aminopyrrolidine backbone have been prepared and characterised. Several systems have been reduced to the salan ONNO type-ligand. All ligands have been complexed to AlIII with Al(1–7)Me, Al(2a)(OiPr) and Al(7a)Me being characterised by single-crystal X-ray diffraction. In general the AlIII centres are best described as being in a trigonal bipyramidal geometry. The solution and solid-state structures are discussed. All complexes have all been trialled for the production of PLA from rac-lactide, the salalen complexes had a preference for heterotactic PLA (Pr = 0.71), whereas the salan had a more isotactic bias (Pm = 0.72). In all cases PLA with low dispersities and predictable molecular weights were prepared. The activity of the two classes of ligands is compared with the salan complexes appearing to be significantly more active than the salalen systems.
Enantioselective Phenolic α-Oxidation Using H2O2 via an Unusual Double Dearomatization Mechanism
McLaughlin, Michael F.,Massolo, Elisabetta,Liu, Shubin,Johnson, Jeffrey S.
supporting information, (2019/02/14)
Feedstock aromatic compounds are compelling low-cost starting points from which molecular complexity can be generated rapidly via oxidative dearomatization. Oxidative dearomatizations commonly rely heavily on hypervalent iodine or heavy metals to provide the requisite thermodynamic driving force for overcoming aromatic stabilization energy. This article describes oxidative dearomatizations of 2-(hydroxymethyl)phenols via their derived bis(dichloroacetates) using hydrogen peroxide as a mild oxidant that intercepts a transient quinone methide. A stereochemical study revealed that the reaction proceeds by a new mechanism relative to other phenol dearomatizations and is complementary to extant methods that rely on hypervalent iodine. Using a new chiral phase-transfer catalyst, the first asymmetric syntheses of 1-oxaspiro[2.5]octa-5,7-dien-4-ones were reported. The synthetic utility of the derived 1-oxaspiro[2.5]octadienones products is demonstrated in a downstream complexity-generating transformation.
3,5-Di-(tert-Butyl)-6-fluoro-cycloSal-d4TMP - A Pronucleotide with a Considerably Improved Masking Group
Ducho, Christian,Wendicke, Silke,Goerbig, Ulf,Balzarini, Jan,Meier, Chris
, p. 4786 - 4791 (2007/10/03)
A new, considerably improved cycloSal masking group has been developed. This new group combines four desirable properties and has been attached to the anti-HIV drug 2′,3′-dideoxy-2′,3′-didehydrothymidine (d4T, 1) to give 3,5-(di-tert-butyl)-6-fluoro-cycloSal-d4TMP (2i). This phosphate triester has a reasonable chemical half-life, highly selectively released d4TMP, has poor - if any - inhibitory effect on butyrylcholinesterase (BChE), and achieved the TK-bypass. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).