Asymmetric alkylation of diphenylmethane derivatives using (-)-sparteine

Wilkinson, JA; Rossington, SB; Leonard, J; Hussain, N

Abstract

Alkylation of 2-oxygenated diphenylmethane derivatives using sec-butyllithium and (−)-sparteine gave enantiomeric excesses of up to 60% with allyl bromide but alkylations with methyl electrophiles were poorly selective. When compounds with a free hydroxy in the 2-position were alkylated the selectivity was reversed.

Citation

Wilkinson, J., Rossington, S., Leonard, J., & Hussain, N. (2004). Asymmetric alkylation of diphenylmethane derivatives using (-)-sparteine. Tetrahedron Letters, 45(6), 1191-1193. https://doi.org/10.1016/j.tetlet.2003.11.138

• Journal Article Type: Article
• Publication Date: Feb 2, 2004
• Deposit Date: Aug 8, 2007
• Journal: Tetrahedron Letters
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 45
• Issue: 6
• Pages: 1191-1193
• DOI: https://doi.org/10.1016/j.tetlet.2003.11.138
• Keywords: Asymmetric, alkylation, deprotonation, diphenylmethane, sparteine
• Publisher URL: http://dx.doi.org/10.1016/j.tetlet.2003.11.138