Beilstein J. Org. Chem.2019,15, 1569–1574, doi:10.3762/bjoc.15.160
acid; cyclopentane; furylcarbinols; PCCP; Introduction
The discovery of a wide range of cyclopentane containing natural products [1][2] and biologically active molecules such as palau’amine [3][4], agelastatin A [5][6][7], pactamycin [8][9][10], and aristeromycin [11][12], has created a demand for new
methodologies to construct this privileged scaffold. The aza-Piancatelli reaction has recently emerged as a particularly attractive method to access densely functionalized cyclopentene cores bearing nitrogen substituents directly from readily available 2-furylcarbinols [13][14][15]. Inspired by Piancatelli’s
when substituted furylcarbinols were used with either para-iodoaniline (2a) or ortho-aminobenzoic acid (2k, Scheme 2). In every case examined, the ortho-aminobenzoic acid gave higher selectivity compared to the corresponding para-iodoaniline, which supports the importance of the additional hydrogen
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Graphical Abstract
Figure 1:
Proposed mechanism of the asymmetric aza-Piancatelli reaction.