Rh-Catalyzed Addition of Arylboroxines to Cyclic N‑(Isopropanesulfinyl)ketimines

Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)­ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalys...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-11, Vol.77 (21), p.9593-9600
Main Authors: Jung, Hyung Hoon, Buesking, Andrew W, Ellman, Jonathan A
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
B derivatives
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Organometalloidal and organometallic compounds
Preparations and properties
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Summary:Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)­ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301634y