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Synfacts 2017; 13(10): 1039
DOI: 10.1055/s-0036-1591304
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Functionalization of Internal Alkenes

Authors

    Contributor(s):

  • Hisashi Yamamoto

  • Yasushi Shimoda

Bayeh L. Le PQ. Tambar UK. * The University of Texas Southwestern Medical Center, Dallas, USA
Catalytic Allylic Oxidation of Internal Alkenes to a Multifunctional Chiral Building Block.

Nature 2017;
547: 196-200
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Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Key words

antimony catalysis - allylic oxidation - hetero-ene reaction

Significance

The authors developed an enantio­selective introduction of electrophilic oxidants into internal alkenes by using a hetero-ene reaction. A Lewis-acid-assisted Brønsted-acid system enables this transformation with high selectivity.


 

Comment

The utility of this transformation was demonstrated by the derivatization of the products to give various valuable chiral compounds. A reaction mechanism is proposed on the basis of mechanistic experiments.


 

 


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