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

作者：Chattopadhyay Shital K^*; Mukherjee Jyoti Prasad

来源：Synthesis (Germany), 2014, 46(18): 2481-2488.

DOI：10.1055/s-0034-1378452

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

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.

• 出版日期2014-9