Cinchona-based primary amine-catalyzed enantioselective aza-Michael reactions of pyrroles with α,β-unsaturated aldehydes

Su Jeong Lee; Jun Gi Ahn; Chang Woo Cho

doi:10.1016/j.tetasy.2014.09.002

Cinchona-based primary amine-catalyzed enantioselective aza-Michael reactions of pyrroles with α,β-unsaturated aldehydes

Su Jeong Lee, Jun Gi Ahn, Chang Woo Cho

Kyungpook National University

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

The cinchona-based primary amine-catalyzed enantioselective aza-Michael reaction of α,β-unsaturated aldehydes with 4,5-dihalo-1H-pyrrole-2-carbonitriles as the N-centered heteroaromatic nucleophile, followed by chemoselective reduction provided the corresponding chiral aza-Michael products in good yields and with excellent enantioselectivities (90-97% ee).

Original language	English
Pages (from-to)	1383-1388
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	25
Issue number	20-21
DOIs	https://doi.org/10.1016/j.tetasy.2014.09.002
State	Published - 31 Oct 2014

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abstract = "The cinchona-based primary amine-catalyzed enantioselective aza-Michael reaction of α,β-unsaturated aldehydes with 4,5-dihalo-1H-pyrrole-2-carbonitriles as the N-centered heteroaromatic nucleophile, followed by chemoselective reduction provided the corresponding chiral aza-Michael products in good yields and with excellent enantioselectivities (90-97% ee).",

author = "Lee, {Su Jeong} and Ahn, {Jun Gi} and Cho, {Chang Woo}",

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AU - Lee, Su Jeong

AU - Ahn, Jun Gi

AU - Cho, Chang Woo

PY - 2014/10/31

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N2 - The cinchona-based primary amine-catalyzed enantioselective aza-Michael reaction of α,β-unsaturated aldehydes with 4,5-dihalo-1H-pyrrole-2-carbonitriles as the N-centered heteroaromatic nucleophile, followed by chemoselective reduction provided the corresponding chiral aza-Michael products in good yields and with excellent enantioselectivities (90-97% ee).

AB - The cinchona-based primary amine-catalyzed enantioselective aza-Michael reaction of α,β-unsaturated aldehydes with 4,5-dihalo-1H-pyrrole-2-carbonitriles as the N-centered heteroaromatic nucleophile, followed by chemoselective reduction provided the corresponding chiral aza-Michael products in good yields and with excellent enantioselectivities (90-97% ee).

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DO - 10.1016/j.tetasy.2014.09.002

M3 - Article

AN - SCOPUS:84908371900

SN - 0957-4166

VL - 25

SP - 1383

EP - 1388

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 20-21

ER -

Cinchona-based primary amine-catalyzed enantioselective aza-Michael reactions of pyrroles with α,β-unsaturated aldehydes

Abstract

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