Discovery of Bifunctional Thiourea/Secondary-Amine Organocatalysts for the Highly Stereoselective Nitro-Mannich Reaction of α-Substituted Nitroacetates

NH group makes all the difference: The highly stereoselective nitro‐Mannich reaction of α‐substituted nitroacetates and N‐Boc aldimines was investigated catalyzed by novel chiral bifunctional thiourea/secondary‐amine systems (an example is shown here). The presence of a basic NH group is crucial f...

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Published in:Chemistry : a European journal 2008-09, Vol.14 (27), p.8094-8097
Main Authors: Han, Bo, Liu, Qing-Ping, Li, Rui, Tian, Xu, Xiong, Xiao-Feng, Deng, Jin-Gen, Chen, Ying-Chun
Format: Article
Language:English
Subjects:
Acetates - chemical synthesis
Acetates - chemistry
amines
Amines - chemistry
Catalysis
Crystallography, X-Ray
Esters - chemical synthesis
Esters - chemistry
hydrogen bonds
Imines - chemistry
Models, Molecular
Molecular Structure
nitro-Mannich reaction
nitroacetate
organocatalysis
Stereoisomerism
thiourea
Thiourea - chemistry
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cited_by cdi_FETCH-LOGICAL-c3810-ecfd2e95db5df044316e80684fd33b77fb826eefafab8d832ab4e3c15d862ec23
cites cdi_FETCH-LOGICAL-c3810-ecfd2e95db5df044316e80684fd33b77fb826eefafab8d832ab4e3c15d862ec23
container_end_page 8097
container_issue 27
container_start_page 8094
container_title Chemistry : a European journal
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creator Han, Bo
Liu, Qing-Ping
Li, Rui
Tian, Xu
Xiong, Xiao-Feng
Deng, Jin-Gen
Chen, Ying-Chun
description NH group makes all the difference: The highly stereoselective nitro‐Mannich reaction of α‐substituted nitroacetates and N‐Boc aldimines was investigated catalyzed by novel chiral bifunctional thiourea/secondary‐amine systems (an example is shown here). The presence of a basic NH group is crucial for the stereocontrol. The products with adjacent quaternary and tertiary chiral centers were directed isolated in moderate to good yields for an array of substrates (91–96 % ee).
doi_str_mv 10.1002/chem.200801170
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subjects Acetates - chemical synthesis
Acetates - chemistry
amines
Amines - chemistry
Catalysis
Crystallography, X-Ray
Esters - chemical synthesis
Esters - chemistry
hydrogen bonds
Imines - chemistry
Models, Molecular
Molecular Structure
nitro-Mannich reaction
nitroacetate
organocatalysis
Stereoisomerism
thiourea
Thiourea - chemistry
title Discovery of Bifunctional Thiourea/Secondary-Amine Organocatalysts for the Highly Stereoselective Nitro-Mannich Reaction of α-Substituted Nitroacetates
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