Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A

Pei Fen Chiang, Wei Sian Li, Jia Hong Jian, Ting Shen Kuo, Ping Yu Wu, Hsyueh Liang Wu

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The unprecedented development of asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines is achieved. This protocol utilizes potassium allyltrifluoroborates and various aldimines to generate enantioenriched homoallylic amines in the presence of 3.0 mol % of Rh(I)/L1b catalyst with up to 90% yield, 98% ee (R = H), and 10:1 diastereoselectivity (R = Me or Ph), yielding the same major diastereomer when using potassium (E)- and (Z)-crotyltrifluoroborate. Its synthetic utility is also illustrated in the total synthesis of (-)-crispine A.

Original languageEnglish
Pages (from-to)158-161
Number of pages4
JournalOrganic Letters
Volume20
Issue number1
DOIs
Publication statusPublished - 2018 Jan 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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