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Published Online September 4, 2008
Science DOI: 10.1126/science.1161976

Reports

Submitted on June 18, 2008
Accepted on August 8, 2008

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

David A. Nicewicz 1 and David W. C. MacMillan 1*

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

* To whom correspondence should be addressed.
David W. C. MacMillan , E-mail: dmacmill{at}princeton.edu

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. Here, we merge 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 and an imidazolidinone organocatalyst. This broadly applicable, yet previously elusive alkylation reaction, is now highly enantioselective and operationally trivial.




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