Asymmetric Synthesis of d-Proline, d-Pipecolic Acid, (2R,3S,4R)-3,4-Dihydroxyproline, and 1,4-Dideoxy-1,4-imino-d-talitol from a Common Precursor

Shital K. Chattopadhyay; Jyoti Prasad Mukherjee

doi:10.1055/s-0034-1378452

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(18): 2481-2488
DOI: 10.1055/s-0034-1378452

paper

Asymmetric Synthesis of d-Proline, d-Pipecolic Acid, (2R,3S,4R)-3,4-Dihydroxyproline, and 1,4-Dideoxy-1,4-imino-d-talitol from a Common Precursor

Shital K. Chattopadhyay*

Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India Fax: +91(33)25828282 eMail: skchatto@yahoo.com

,

Jyoti Prasad Mukherjee

Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India Fax: +91(33)25828282 eMail: skchatto@yahoo.com

› Institutsangaben

Abstract

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Abstract

Methodology involving stereoselective aza-Michael addition and ring-closing metathesis as key steps has been developed for the preparation of (2R)-pipecolic acid, (2R)-proline, (2R,3S,4R)-3,4-dihydroxyproline, and the known glycosidase inhibiting azasugar 1,4-dideoxy-1,4-imino-d-talitol from a common starting material namely (R)-cyclohexylideneglyceraldehyde in good overall yields.

Key words

amino acids - chiral pool - metathesis - Michael addition - stereoselective synthesis

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Referenzen

References

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