Stereoselective Synthesis of Densely Functionalized Pyrrolidin-2-ones by a Conjugate Addition/Nitro-Mannich/Lactamization Reaction
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https://figshare.com/articles/dataset/Stereoselective_Synthesis_of_Densely_Functionalized_Pyrrolidin_2_ones_by_a_Conjugate_Addition_Nitro_Mannich_Lactamization_Reaction/2503420
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资源简介：
Copper-catalyzed conjugate addition of diorgano zinc
reagents to
nitroacrylate 1 followed by a subsequent nitro-Mannich
reaction and in situ lactamization leads to an efficient
one-pot synthesis of 1,3,5-trisubstituted 4-nitropyrrolidin-2-ones
(5). The versatility of the reaction is shown for a wide
range of N-p-(methoxy)phenyl protected
aldimines 3 derived from alkyl, aryl, and heteroaryl
aldehydes. The densely functionalized pyrrolidin-2-ones 5 are isolated as single diastereoisomers (40 examples, 33–84%
yield). An enantioselective copper-catalyzed conjugate addition of
diethylzinc led to highly crystalline products that could be recrystallized
to enantiopurity in high yield. A range of successful chemoselective
transformations were investigated, which widens the applicability
of the pyrrolidn-2-ones as stereochemically pure building blocks for
further organic synthesis.
创建时间：
2012-07-20
