Asymmetric Organocatalytic Formal Aza-Michael Addition of Ammonia to Nitroalkenes

The formal addition of ammonia to nitroalkenes, affording optically active β‐amino nitro compounds in high yields and enantioselectivities, is presented (see scheme). The approach is based on a novel thiourea‐catalyzed aza‐Michael reaction, by which benzophenone imine serves as a masked ammonia equi...

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Veröffentlicht in:	Chemistry : a European journal 2010-12, Vol.16 (45), p.13330-13334
Hauptverfasser:	Lykke, Lennart, Monge, David, Nielsen, Martin, Jørgensen, Karl Anker
Format:	Artikel
Sprache:	eng
Schlagworte:	alkenes Alkenes - chemical synthesis Alkenes - chemistry Ammonia - chemistry Benzophenones - chemistry Catalysis Chemistry Combinatorial Chemistry Techniques Hydrolysis Imines - chemistry Michael addition Molecular Structure Nitro Compounds - chemical synthesis Nitro Compounds - chemistry nitroalkenes organocatalysis Stereoisomerism Thiourea - chemistry
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creator	Lykke, Lennart Monge, David Nielsen, Martin Jørgensen, Karl Anker
description	The formal addition of ammonia to nitroalkenes, affording optically active β‐amino nitro compounds in high yields and enantioselectivities, is presented (see scheme). The approach is based on a novel thiourea‐catalyzed aza‐Michael reaction, by which benzophenone imine serves as a masked ammonia equivalent, which is released by hydrolysis.
doi_str_mv	10.1002/chem.201002415
format	Article
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subjects	alkenes Alkenes - chemical synthesis Alkenes - chemistry Ammonia - chemistry Benzophenones - chemistry Catalysis Chemistry Combinatorial Chemistry Techniques Hydrolysis Imines - chemistry Michael addition Molecular Structure Nitro Compounds - chemical synthesis Nitro Compounds - chemistry nitroalkenes organocatalysis Stereoisomerism Thiourea - chemistry
title	Asymmetric Organocatalytic Formal Aza-Michael Addition of Ammonia to Nitroalkenes
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