Asymmetric Dihydroxylations of Enynes with a Trisubstituted C=C Bond. An Unprecedented Route to γ-Lactone Building Blocks with a Quaternary Stereocenter

被引：5
|
作者：
Burghart-Stoll, Heike [1 ]
Kapferer, Tobias [2 ]
Brueckner, Reinhard [1 ]
机构：
[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany
[2] Bayer CropSci AG, D-40789 Monheim, Germany
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 05期
关键词：
ENANTIOSELECTIVE SYNTHESIS; TRICHODERMA-LONGIBRACHIATUM; ABSOLUTE STEREOCHEMISTRY; TETRONIC ACID; LIGAND CLASS; ALCOHOLS; CONFIGURATION; METABOLITES; REARRANGEMENT; CAROTENOIDS;
D O I：
10.1021/ol103061g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
En route to a comprehensive set of hydroxylactone building blocks (4R,5R)-, (4R,5S)-, (4S,5R)-, and (4S,5S)-5a, Sharpless asymmetric dihydroxylations of allylic chlorides (E)- and (2)-9 were performed. They delivered the four stereoisomers of diol 10 with up to 92% ee and absolute configurations, which were proven to be in accordance with the Sharpless mnemonic.
引用
收藏
页码：1016 / 1019
页数：4
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