2009
DOI: 10.1002/adsc.200800734
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Elucidation of Architectural Requirements from a Spacer in Supported Proline‐Based Catalysts of Enantioselective Aldol Reaction

Abstract: In order to delineate the properties of the spacer architecture responsible for the strong positive dendritic effect exhibited by polymer-supported proline-based catalysts, we prepared two series of polystyrene-bound model catalysts. The first series was based on a linear and partially dendritic spacers (of reduced branching and valency) imitating the length of the second generation spacer, while the second series was based on the first generation dendron spacer with one functional (proline-terminated) and one… Show more

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Cited by 32 publications
(11 citation statements)
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“…The synthesis of the potential catalyst G0(Pro, Gua-Boc 2 ) (6) is depicted in Scheme 1. It is based on the immobilization of the heteroarm branching unit, methyl 3-hydroxy-5-hydroxymethylbenzoate, [6] on its conversion into monoprotected diol 2, and on the stepwise assembly of the arms: first the trisalkoxycarbonyl guanidine arm and then the proline arm.…”
Section: Resultsmentioning
confidence: 99%
“…The synthesis of the potential catalyst G0(Pro, Gua-Boc 2 ) (6) is depicted in Scheme 1. It is based on the immobilization of the heteroarm branching unit, methyl 3-hydroxy-5-hydroxymethylbenzoate, [6] on its conversion into monoprotected diol 2, and on the stepwise assembly of the arms: first the trisalkoxycarbonyl guanidine arm and then the proline arm.…”
Section: Resultsmentioning
confidence: 99%
“…[35][36][37][38][39][40][41] Whereas the assembly of the hydrophobic branchesi sa chieved via the reductiono ft he ester groups of this scaffold, three different synthetic routes were examined for the introduction of the imidazole moiety near the focal point of the future dendron (the phenol hydroxy function). [35][36][37][38][39][40][41] Whereas the assembly of the hydrophobic branchesi sa chieved via the reductiono ft he ester groups of this scaffold, three different synthetic routes were examined for the introduction of the imidazole moiety near the focal point of the future dendron (the phenol hydroxy function).…”
Section: Resultsmentioning
confidence: 99%
“…Our synthesis is based on methyl 3‐hydroxy‐5‐hydroxymethyl benzoate ( 1 ), a trifunctional building block, whose preparation and use in solid‐phase synthesis was recently described by us 12. This unit can be immobilized on halobenzyl functionalized resin (e.g., as the first building block on Wang Bromo polystyrene, Scheme ).…”
Section: Resultsmentioning
confidence: 99%