4.7 Article

Construction of Optically Active 2H- and 3H-Pyrroles by Cyclization and Chirality Maintaining 1,5-Ester Shift Reactions

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 16, Pages 3744-3750

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900481

Keywords

2H-Pyrroles; 3H-Pyrroles; Ester shift reaction; Chirality maintaining; Asymmetric synthesis; Magnesium catalysis

Funding

  1. NSFC [21602091, 21432003, 81473095]
  2. Fundamental Research Funds [lzujbky-2019-68, 2018-kb11, 2017-19, 2017-118]

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Construction of enantioenriched 2H- and 3H-pyrroles are achieved in current work by using readily available alpha-isocyanoacetates and alkynyl ketones as precursors. To realize the asymmetric synthesis of 2H-pyrroles, a proper in situ generated magnesium catalytic method was developed. On the other hand, the discovery of an aluminium mediated chirality maintaining 1,5-ester shift reaction promoted the successful synthesis of enantioenriched 3H-pyrroles.

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