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

页码：1016 / 1019

页数：4

共 2 条

[1] Merging allylic C-H bond activation and C-C bond cleavage en route to the formation of a quaternary carbon stereocenter in acyclic systems
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