کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5218139 1383317 2013 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Stereoselective synthesis of α-methylenecyclopentenones via a Diels–Alder/retro-Diels–Alder protocol
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Stereoselective synthesis of α-methylenecyclopentenones via a Diels–Alder/retro-Diels–Alder protocol
چکیده انگلیسی

A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels–Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels–Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers.

Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 69, Issue 44, 4 November 2013, Pages 9270–9276