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A stereocontrolled synthesis of cis-3,4-diarylisochroman-1-ones through diastereoselective reaction of benzaldehydes and α-lithio-2-cyanodiarylmethane intermediates.

✍ Scribed by Lori Crenshaw; Subhash P. Khanapure; Upali Siriwardane; Edward R. Biehl

Book ID
104217555
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
215 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

A highly dlastereoselectlve reacnon of benzaldehydes and a-hdn+2cyanmhnethanes IS reported Usmg thus approach a stereocontrolled synthesis of crs-3,4duxyhsochroman-l-ones IS described..

Recently we obsemedl that the reacuon of arynes (2) generated from 2-bromoanisoles (1) and hthuun ddsopropylarmde ~th hth~o axyl-mtnles led to the formanon of polysubsmuted benzenes (6) vza tandem ad&non rearrangement In the course of dus work,1 the a-kti~2-cyan&arylmethanes

(5) obtamed appeared to be valuable mtermeihates for electroptic quenching. By tcappmg them wnh electrophties, compounds could be produced possessmg the ortho tiunchonahty.

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✍ Kiran Matcha; Subrata Ghosh 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 119 KB

A general stereocontrolled approach for entry into a family of highly biologically active 2,5-diaryl-3,4-disubstituted furano lignans has been developed. The key step involves a diastereoselective aldol-type condensation of an ester enolate having an a-chiral center with an aromatic aldehyde. The me