Catalytic Enantioselective Aza-Piancatelli Rearrangement

Huilin Li; Rongbiao Tong; Jianwei Sun

doi:10.1002/anie.201607714

Catalytic Enantioselective Aza-Piancatelli Rearrangement

Angew Chem Int Ed Engl. 2016 Nov 21;55(48):15125-15128. doi: 10.1002/anie.201607714. Epub 2016 Oct 27.

Authors

Huilin Li¹, Rongbiao Tong¹, Jianwei Sun¹

Affiliation

¹ Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.

PMID: 27785871
DOI: 10.1002/anie.201607714

Abstract

An efficient organocatalytic enantioselective aza-Piancatelli rearrangement is disclosed. The powerful process provides rapid access to valuable chiral 4-amino-2-cyclopentenone building blocks from readily available 2-furfurylcarbinols with excellent chemo-, enantio-, and diastereoselectivities under mild reaction conditions.

Keywords: asymmetric catalysis; carbocycles; cyclization; organocatalysis; rearrangements.

Publication types

Research Support, Non-U.S. Gov't