Di-l-menthyl (acetoxymethylene)malonate, a new chiral dienophile: enantioselective route to carbocyclic analogs of C-nucleoside

Titanium tetrachloride promoted Diels-Alder reaction of new chiral dienophile, di-l-menthyl (acetoxymethylene)malonate, with cyclopentadiene not only proceeds with high diastereofacial selectivity but also provides an efficient enantioselective synthetic route to carbocyclic analogues of C-nucleosid...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 53; no. 1; pp. 226 - 227
Main Authors Katagiri, Nobuya, Haneda, Toru, Hayasaka, Etusko, Watanabe, Nobuhisa, Kaneko, Chikara
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.01.1988
Amer Chemical Soc
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Stereoisomer
Enantioselectivity
Diels Alder addition
Lactone
Chiral compound
Oxygen heterocycle
Titanium IV Chlorides
Geminal compound
Dienophile
Six membered ring
Absolute configuration
Diester
Bicyclic compound
Monoterpene
Secondary alcohol
Acylate
Monocyclic compound
Ethylenic compound
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Summary:Titanium tetrachloride promoted Diels-Alder reaction of new chiral dienophile, di-l-menthyl (acetoxymethylene)malonate, with cyclopentadiene not only proceeds with high diastereofacial selectivity but also provides an efficient enantioselective synthetic route to carbocyclic analogues of C-nucleoside.
Bibliography:ark:/67375/TPS-XVMG9HNB-W
istex:A76AF7B55763326FD431316C68780A752D4F39B9
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00236a057