Stereoselective synthesis of piperidine-2,6-dicarboxylic acids by photocatalytic reaction of aqueous cadmium(II) sulfide dispersion

Photoirradiation at wavelength > 300 nm onto a deaerated aqueous suspension of cadmium(II) sulfide (CdS) particles in an aqueous solution of a mixture of stereo isomers of 2,6-diamiopimelic acid (DAP) produced piperidine-2,6-dicarboxylic acid (PDC). Both yield and trans cis ratio of PDC markedly...

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Bibliographic Details
Published inTetrahedron letters Vol. 36; no. 18; pp. 3189 - 3192
Main Authors Ohtani, Bunsho, Kusakabe, Satoshi, Okada, Katsumi, Tsuru, Shigeto, Izawa, Kunisuke, Amino, Yusuke, Nishimoto, Sei-ichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.05.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PIPERIDINES
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Summary:Photoirradiation at wavelength > 300 nm onto a deaerated aqueous suspension of cadmium(II) sulfide (CdS) particles in an aqueous solution of a mixture of stereo isomers of 2,6-diamiopimelic acid (DAP) produced piperidine-2,6-dicarboxylic acid (PDC). Both yield and trans cis ratio of PDC markedly depended on the kind of CdS photocatalysts, its pre-treatment, and loading of fine platinum particles. A CdS photocatalyst prepared by heat-treatment at 1023 K in the presence of a small amount of air showed the highest yield and trans cis ratio. CdS suspensions photocatalyzed the stereoselective deamino-N-cyclization of 2,6-diaminopimelic acid.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)00509-B