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. 2010 Dec 8;132(48):17108-10.
doi: 10.1021/ja108949w. Epub 2010 Nov 15.

Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides

Deidre L Sandrock  1 , Ludivine Jean-Gérard, Cheng-yi Chen, Spencer D Dreher, Gary A Molander
Affiliations

Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides

Deidre L Sandrock et al. J Am Chem Soc. .

Abstract

The stereospecific cross-coupling of enantioenriched nonbenzylic secondary alkyl boron compounds has been achieved. The high selectivity toward product formation over an undesired β-H elimination pathway is achieved via an intramolecular coordination of an ancillary carbonyl to the metal center in the diorganopalladium intermediate.

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Figures

Scheme 1
Scheme 1
Preparation and Cross-Coupling of Enantioenriched β-Trifluoroboratoamide
Scheme 2
Scheme 2
Proposed Mechanism for Complete Stereochemical Inversion
See this image and copyright information in PMC

References

    1. These authors contributed equally to this work.

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