Synergistic effects within a C2-symmetric organocatalyst : the potential formation of a chiral catalytic pocket

Delaney, Joshua P., Brozinski, Hannah L. and Henderson, Luke C. 2013, Synergistic effects within a C2-symmetric organocatalyst : the potential formation of a chiral catalytic pocket, Organic and biomolecular chemistry, vol. 11, no. 18, pp. 2951-2960.

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Title Synergistic effects within a C2-symmetric organocatalyst : the potential formation of a chiral catalytic pocket
Author(s) Delaney, Joshua P.
Brozinski, Hannah L.
Henderson, Luke C.
Journal name Organic and biomolecular chemistry
Volume number 11
Issue number 18
Start page 2951
End page 2960
Total pages 10
Publisher Royal Society of Chemistry
Place of publication Cambridge, England
Publication date 2013
ISSN 1477-0520
1477-0539
Summary This study describes the synthesis of five novel C2-symmetric organocatalysts that facilitate the on-water asymmetric aldol reaction at low catalyst loading (1 mol%) without the use of additives. Each catalyst is composed of two diprolinamide units joined by a symmetric alkyl bridging group allowing for systematic modulation of catalytic site proximity. Typically, catalysts in this manuscript which bear the catalytic units in close proximity gave the best reaction outcomes in terms of conversion (up to >99%), diastereomeric ratio (4/96, syn/anti) and enantiomeric excess (up to 97%). This effect has been attributed to the assembly of a chiral pocket, facilitated by hydrogen bonding at the oil-in-water interface.
Language eng
Field of Research 059999 Environmental Sciences not elsewhere classified
Socio Economic Objective 970105 Expanding Knowledge in the Environmental Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Persistent URL http://hdl.handle.net/10536/DRO/DU:30055446

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