Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/55699
Title: Highly enantioselective synthesis of γ-nitro heteroaromatic ketones in a doubly stereocontrolled manner catalyzed by bifunctional thiourea catalysts based on dehydroabietic amine : a doubly stereocontrolled approach to pyrrolidine carboxylic acids
Authors: Jiang, XX
Zhang, YF
Chan, ASC
Wang, R
Issue Date: 2009
Publisher: American Chemical Society
Source: Organic letters, 2009, v. 11 , no. 1, p. 153-156 How to cite?
Journal: Organic letters 
Abstract: A new class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was investigated for the first time, affording (S)-or (R)-γ-nitro heteroaromatic ketones with excellent enantioselectivities (up to ee >99%). Furthermore, the nearly optically pure γ-nitro heteroaromatic ketones can be readily transformed into chiral pyrrolidine carboxylic acids.
URI: http://hdl.handle.net/10397/55699
ISSN: 1523-7060
EISSN: 1523-7052
DOI: 10.1021/ol8025268
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