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Originally published in Science Express on 4 September 2008
Science 3 October 2008:
Vol. 322. no. 5898, pp. 77 - 80
DOI: 10.1126/science.1161976
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Reports

Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes

David A. Nicewicz and David W. C. MacMillan*

Photoredox catalysis and organocatalysis represent two powerful fields of molecule activation that have found widespread application in the areas of inorganic and organic chemistry, respectively. We merged these two catalysis fields to solve problems in asymmetric chemical synthesis. Specifically, the enantioselective intermolecular {alpha}-alkylation of aldehydes has been accomplished using an interwoven activation pathway that combines both the photoredox catalyst Ru(bpy)3Cl2 (where bpy is 2,2'-bipyridine) and an imidazolidinone organocatalyst. This broadly applicable, yet previously elusive, alkylation reaction is now highly enantioselective and operationally trivial.

Contribution from Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.

* To whom correspondence should be addressed. E-mail: dmacmill{at}princeton.edu

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Science. ISSN 0036-8075 (print), 1095-9203 (online)