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Synfacts 2007(4): 0431-0431
DOI: 10.1055/s-2007-968347
DOI: 10.1055/s-2007-968347
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Organocatalytic Asymmetric Synthesis of Tertiary Alkyl Chlorides
E. C. Lee, K. M. McCauley, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968347-1.jpg)
Significance
An organocatalytic asymmetric synthesis of tertiary alkyl chlorides has been developed. Planar chiral (-)-PPY* (3 mol%) mediates the addition of 2,2,6,6-tetrachlorocyclohexanone (2) to ketenes 1 to give tertiary α-chloro esters 3 in good yields and enantioselectivities. Enol ester 4 has been transformed into the corresponding methyl ester 5 and alcohol 6 in acceptable yields and with preservation of the stereochemistry. Furthermore, mechanistic considerations based on NMR spectroscopy and experimental data are provided.