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Synfacts 2017; 13(10): 1052
DOI: 10.1055/s-0036-1591303
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Titanium-Catalyzed Enantioselective S-Oxidation of 1,5-Benzothiazepines

Contributor(s):
Hisashi Yamamoto
,
Wataru Muramatsu
Makino K. Yoneda T. Ogawa R. Kanase Y. Tabata H. Oshitari T. Natsugari H. Takahashi H. * Teikyo University, Tokyo, Japan
Catalytic Asymmetric S-Oxidation of N-Benzoyl-1,5-benzothiazepines.

Tetrahedron Lett. 2017;
58: 2885-2888
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Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Key words

titanium catalysis - diethyl tartrate - oxidation - benzothiazepines

Significance

The (E,aS,1S)-sulfoxide of N-benzoyl-1,5-benzothiazepines are recognized by ­vasopressin receptors. The authors have developed an efficient catalytic method for the asymmetric S-oxidation of N-benzoyl-1,5-benzothiazepines with a chiral titanium tartrate complex.


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Comment

This Ti-catalyzed S-oxidation provides optically active N-benzoyl-1,5-benzothiazepines, which act as vasopressin receptors, with high yields and excellent enantioselectivities.


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