Bis(mandelato)borate: an effective, inexpensive spiroborate anion for chiral resolutionElectronic supplementary information (ESI) available: Synthesis and characterization data. CCDC 1054443, 897202-897204. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5cc04977f

• Main Authors: Wong, Lawrence W-Y, Kan, Jack W-H, Nguyen, Thanh-ha, Sung, Herman H-Y, Li, Dang, Au-Yeung, Alex S-F, Sharma, Rajpal, Lin, Zhenyang, Williams, Ian D
• Format: Journal Article
• Language: English
• Published: 20.10.2015
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c5cc04977f

Bis(mandelato)borate [B(Man) 2 ] − ( R - or S -) anions are simply prepared and appear widely effective for resolution of racemic cations. Three examples demonstrate their scope; the alkaloid tetrahydropalmatine (THP), 1,2-diaminopropane (1,2-dap) and the metal-organic complex [Co(phen) 3 ] 3+ are readily resolved, either by a facile one-pot procedure, or via counter-ion metathesis. Cations of tetrahydropalmatine (THP), 1,2-diaminopropane (1,2-dap) and [Co(phen) 3 ] 3+ are all readily resolved by the red [B S ( R -Man) 2 ] anions with >90% ee in 1 easy step.