兰州大学机构库 >生命科学学院
2-甲基-1-丁烯-3-炔对醛的不对称加成反应研究
Alternative TitleStudy on the catalytic asymmetric addition of 2-methyl-1-butene-3-yne to aldehydes
胡国文
Thesis Advisor王锐
2009-05-27
Degree Grantor兰州大学
Place of Conferral兰州
Degree Name硕士
Keyword 2-甲基-1-丁烯-3-炔 不对称催化 β-磺酰胺基醇
Abstract末端炔对羰基化合物的不对称加成反应是一种非常重要的构建手性炔丙醇的方法,其产生的手性炔丙醇是很多天然产物、手性药物的重要中间体。近年来,末端炔对羰基化合物的不对称加成反应取得了很大的进展,但研究主要集中在苯乙炔对羰基化合物的加成反应上。而含有官能团的炔对羰基化合物的加成除了含有羟基和炔基这两个很重要的官能团之外,还含有新的官能团,所以在天然产物和手性药物等有机分子合成中有着更广泛的应用前景。这也是当前和以后一段时间内,该领域研究热点之一。该论文主要论述了2-甲基-1-丁烯-3炔对醛的不对称加成反应研究。 2-甲基-1-丁烯-3炔分子中的双键,在化学反应中能够发生多种化学转化,其对羰基化合物的催化不对称加成产物有着很高的应用价值。另外,2-甲基-1-丁烯-3炔与苯乙炔相比,其酸性不同,分子也小一点,这就导致了它们与羰基化合物加成反应与苯乙炔的不同。 我们从天然L-苯丙氨基酸出发,经过简单步骤,合成出β-磺酰胺基醇配体L1,并将其应用于2-甲基-1-丁烯-3炔对醛的不对称加成反应,对醛的加成反应产率最高达到78%,ee值最高达到86%。
Other AbstractAddition of metallated terminal alkynes to carbonyls is considered as an effective route for the synthesis of chiral propargyl alcohols and has gained considerable significance in recent years.And Optically active propargyl alcohols are important and versatile building blocks for the synthesis of a wide range of pharmaceuticals and natural products. For the possible further transformations of functionalized group, the asymmetric addition of 2-methyl-1-butene-3-yne to aldehydes should have more potential applications than phenylacetylene for the synthesis of complex bioactive natural products. Herein we mainly discuss design and synthesis of some chiral ligands or catalysts and their application to the asymmetric addition of 2-Methyl-1-butene-3-yne to aldehydes. Double bond in the molecular of 2-methyl-1-butene-3-yne have many Variability. Addition of 2-methyl-1-butene-3-yne to carbonyls have big value.Also it is different with phenylacetylene,such as smaller and acidity,which result that its addition to carbonyls is different withPhenylacetylene to carbonyls. Sulfonamide ligand 6a and 6b was easily prepared in three simple steps and applied in the enantioselective addition of 2-methyl-1-butene-3-yne to aldehydes. The corresponding chiral tertiary propargylic alcohols were obtained with enantiomeric excesses of up to 86% , yield of 78% under very mild conditions.
URL查看原文
Language中文
Document Type学位论文
Identifierhttps://ir.lzu.edu.cn/handle/262010/222090
Collection生命科学学院
Recommended Citation
GB/T 7714
胡国文. 2-甲基-1-丁烯-3-炔对醛的不对称加成反应研究[D]. 兰州. 兰州大学,2009.
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