LDA-Mediated Selective Addition Reaction of Vinylidenecyclopropanes with Aldehydes, Ketones, and Enones: Facile Synthesis of Vinylcyclopropenes, Allenols, and 1,3-Enynes
摘要:
Highly selective addition reaction of vinylidenecyclopropanes 1 was realized by treatment with LDA in THF and quenching with aldehydes, ketones, and enones. A number of vinylcyclopropenes, allenols, and 1,3-enynes were obtained selectively in moderate to good yields depending on the nature of different electrophiles.
LDA-Mediated Cascade Carbolithiation Reactions of Vinylidenecyclopropanes with Enones and N-Sulfonated Imines as well as Nitroalkene and (Phenylmethylidene)malononitrile
作者:Bei-Li Lu、Jian-Mei Lu、Min Shi
DOI:10.1002/ejoc.201101403
日期:2012.1
LDA-mediatedcascadecarbolithiationreactions of vinylidenecyclopropanes with enones and N-sulfonatedimines as well as nitroalkene and (phenylmethylidene)malononitrile in THF at –78 °C have been realized; the corresponding novel adducts were produced in moderate to good yields with moderate to high diastereoselectivities. The scope and limitations are discussed as well as a plausible reaction mechanism
A Catalytic Method for the Preparation of Polysubstituted Cyclopentanes: [3+2] Cycloaddition of Vinylidenecyclopropanes with Activated Olefins Catalyzed by Triflic Imide
作者:Wei Li、Min Shi
DOI:10.1021/jo802294s
日期:2009.1.16
[3+2] Cycloadditions of vinylidenecyclopropanes (VDCPs) with electron-deficient olefins, such as methyl vinyl ketone (MVK) and acrylaldehyde, proceed smoothly in the presence of a catalytic amount of triflic imide (Tf2NH) to give the corresponding functionalized cyclopentanes in good to high yields.
LDA-mediated domino carbolithiation reactions of vinylidenecyclopropanes with but-3-yn-2-one and 1-phenylprop-2-yn-1-one
作者:Bei-Li Lu、Jian-Mei Lu、Min Shi
DOI:10.1016/j.tetlet.2009.11.012
日期:2010.1
A novel domino carbolithiation reaction of vinylidenecyclopropanes 1 with but-3-yn-2-one and 1-phenylprop-2-yn-1-one by treating with LDA in THF was observed to give the corresponding adducts in moderate to good yields. The scope and limitations as well as the plausible mechanism have been discussed on the basis of control experiments. (C) 2009 Elsevier Ltd. All rights reserved.
LDA-Mediated Selective Addition Reaction of Vinylidenecyclopropanes with Aldehydes, Ketones, and Enones: Facile Synthesis of Vinylcyclopropenes, Allenols, and 1,3-Enynes
作者:Jian-Mei Lu、Min Shi
DOI:10.1021/ol800463k
日期:2008.5.1
Highly selective addition reaction of vinylidenecyclopropanes 1 was realized by treatment with LDA in THF and quenching with aldehydes, ketones, and enones. A number of vinylcyclopropenes, allenols, and 1,3-enynes were obtained selectively in moderate to good yields depending on the nature of different electrophiles.