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J Org Chem. 2012 Nov 2;77(21):9593-600. doi: 10.1021/jo301634y. Epub 2012 Oct 24.

Rh-catalyzed addition of arylboroxines to cyclic N-(isopropanesulfinyl)ketimines.

Author information

1
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.

Abstract

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.

PMID:
23094717
DOI:
10.1021/jo301634y

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