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从两个醛和亚甲基三苯膦出发,通过汇聚合成共轭 1,2-二取代 E-烯丙醇。

Convergent synthesis of conjugated 1,2-disubstituted E-allylic alcohols from two aldehydes and methylenetriphenylphosphorane.

机构信息

Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.

出版信息

Org Biomol Chem. 2012 Oct 21;10(39):7949-51. doi: 10.1039/c2ob26346g. Epub 2012 Aug 30.

DOI:10.1039/c2ob26346g
PMID:22936294
Abstract

β-Lithiooxyphosphonium ylides, made in situ from an aldehyde and methylenetriphenylphosphorane, react with a second aldehyde to form E-allylic alcohols. α-Branching and α,β-unsaturation in the second aldehyde, together with the lack of further substitution on the phosphorane carbon play important roles in selectivity. A range of these aldehydes, in addition to aromatic aldehydes as the second aldehyde also provided synthetically useful access to E-allylic alcohols.

摘要

β-锂氧磷叶立德由醛和亚甲基三苯膦原位反应制得,与第二个醛反应生成 E-烯丙醇。第二个醛中的α-支链和α,β-不饱和性,以及磷叶立德碳上缺乏进一步取代,对选择性起着重要作用。除了芳香醛作为第二个醛外,这些醛中的一系列化合物也为 E-烯丙醇的合成提供了有用的途径。

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引用本文的文献

1
Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine.由三苯基膦捕获α-锂化末端环氧化物生成的β-锂氧磷叶立德的烯烃。
Beilstein J Org Chem. 2012;8:1896-900. doi: 10.3762/bjoc.8.219. Epub 2012 Nov 7.