Conformational preference and remote (1,10) stereocontrol in biphenyl-2,2′-dicarboxamides

Jonathan Clayden*, Andrew Lund, Latifa H. Youssef

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

37 Citations (Scopus)

Abstract

(Matrix Presented) The double ortholithiation and electrophilic quench of N,N,N′N′-tetraisopropylbiphenyl-2,2′-dicarboxamide 1 is diastereoselective, giving the chiral C2-symmetric atropisomers of the 3,3′-disubstituted products 3. These chiral atropisomers can be converted with moderate to good stereoselectivity to their achiral, centrosymmetric epimers by heating. The stereoselectivity of the double lithiation-quench reaction is determined by the stereochemistry of the intermediate doubly lithiated species 2, either diastereoisomer of which may be formed stereospecfically from the corresponding atropisomeric dibromo compounds.

Original languageEnglish
Pages (from-to)4133-4136
Number of pages4
JournalOrganic Letters
Volume3
Issue number26
Early online date27 Nov 2001
DOIs
Publication statusPublished - 27 Dec 2001

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