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Synfacts 2017; 13(06): 0601
DOI: 10.1055/s-0036-1590457
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Palladium(II)-Catalyzed Borylation

Contributor(s):
Hisashi Yamamoto
,
Yasushi Shimoda
He J. Shao Q. Wu Q. Yu J.-Q. * The Scripps Research Institute, La Jolla, USA
Pd(II)-Catalyzed Enantioselective C(sp3)–H Borylation.

J. Am. Chem. Soc. 2017;
139: 3344-3347
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Further Information

Publication History

Publication Date:
16 May 2017 (online)

 
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Key words

palladium catalysis - borylation - amides

Significance

The authors developed a palladium(II)-catalyzed borylation of cyclic amides by using chiral bidentate ligands. A wide variety of borylated cyclobutanes bearing an amide group were obtained with high selectivities.


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Comment

A transformation of the product, including the removal of the amide auxiliary, was accomplished to demonstrate the synthetic utility of the reaction. An asymmetric induction model is also proposed.


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