Efficient synthesis of chiral C2-symmetric diamines via allylboration of bis-N,N′-metallodiimines

✍ Scribed by P. Veeraraghavan Ramachandran; Debanjan Biswas; Marek P. Krzeminski; Guang-Ming Chen

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 425 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.11.013

✦ Synopsis

An enantioselective synthesis of C 2 -symmetric bis-homoallylic aromatic and heteroaromatic diamines in 54-89% yields, in 73-94% de and P98% ee has been achieved via the allylboration of the corresponding N,N 0 -bis(trimethylsilyl)dialdimines and N,N 0 -bis(diisobutylalumino)dialdimines with B-allyldiisopinocampheylborane in the presence of methanol, followed by alkaline hydrogen peroxide workup. One-pot synthesis of stable N,N 0 -bis(benzaldimine-triethylborane) complexes and subsequent allylboration to afford benzene diamines is also described.