Optical resolution, stereoselective synthesis, and crystal structure of 9α-(3-azabicyclo[3,3,1]nonanyl)-2′cyclopentyl-2′-hydroxy- 2′-phenylacetate

Yan Qing Liu, He Liu*, Bo Hua Zhong, Yu Lin Deng, Ke Liang Liu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

9α-(3-Azabicyclo[3,3,1 ]nonanyl)-2′-cyclopentyl-2′- hydroxy-2′-phenylacetate (1) was synthesized and its enantiomers were obtained by the optical resolution of racemates with the chiral host N-p-toluenesulfonylglutamic acid. Optical pure 1 was also effective diastereoselective synthesized using benzaldehye as steric hindrance agent from the chiral starting material, (S) or (R)-mandelic acid. The structure of the title compound was first elucidated by X-ray analysis.

Original languageEnglish
Pages (from-to)1403-1412
Number of pages10
JournalSynthetic Communications
Volume35
Issue number10
DOIs
Publication statusPublished - 2005

Keywords

  • Crystal structure
  • Optical resolution
  • Stereoselective synthesis

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