Asymmetric Synthesis of Highly Substituted β-Lactones by Nucleophile-Catalyzed [2+2] Cycloadditions of Disubstituted Ketenes with Aldehydes†
Jonathan E. Wilson
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Fax: (+1) 617-324-3611
Search for more papers by this authorGregory C. Fu Prof. Dr.
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Fax: (+1) 617-324-3611
Search for more papers by this authorJonathan E. Wilson
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Fax: (+1) 617-324-3611
Search for more papers by this authorGregory C. Fu Prof. Dr.
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Fax: (+1) 617-324-3611
Search for more papers by this authorWe thank Ivory D. Hills for X-ray crystallographic studies. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences: R01-GM57034; National Cancer Institute: training grant CA009112), Merck, and Novartis. Funding for the MIT Department of Chemistry Instrumentation Facility has been furnished in part by NSF CHE-9808061 and NSF DBI-9729592.
Graphical Abstract
α,α-Disubstituted β-lactones can be obtained by the cycloaddition of the corresponding ketenes with aldehydes (see scheme). For the first time, a chiral PPY derivative, 1, serves as an efficient catalyst for the asymmetric synthesis of β-lactones (PPY=4-pyrrolidin-1-ylpyridine). To date, this is the only catalyst that is effective for enantioselective cycloadditions of disubstituted ketenes with aldehydes.
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