Synthesis of new, highly hindered C-2-symmetric trans (2S,5S)-disubstituted pyrrolidines

VK Aggarwal*, Franck J Sandrinelli, JPH Charmant

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

Abstract

trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Article numberPII S0957-4166(02)00032-0
Pages (from-to)87-93
Number of pages7
JournalTetrahedron: Asymmetry
Volume13
Issue number1
Publication statusPublished - 13 Feb 2002

Keywords

  • DIELS-ALDER REACTION
  • ALPHA-AMINO-ACIDS
  • ASYMMETRIC-SYNTHESIS
  • TRANS-2,5-DISUBSTITUTED PYRROLIDINES
  • CHIRAL AUXILIARIES
  • D-MANNITOL
  • 2,5-DISUBSTITUTED PYRROLIDINES
  • ENANTIOSELECTIVE SYNTHESIS
  • CLAISEN REARRANGEMENTS
  • NUCLEOPHILIC-ADDITION

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