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

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 r...

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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
LanguageEnglish
Published 20.10.2015
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Abstract 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.
AbstractList 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.
Author Sharma, Rajpal
Nguyen, Thanh-ha
Au-Yeung, Alex S-F
Kan, Jack W-H
Sung, Herman H-Y
Wong, Lawrence W-Y
Li, Dang
Williams, Ian D
Lin, Zhenyang
AuthorAffiliation Department of Chemistry
The Hong Kong University of Science and Technology
Panjab University
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Notes For ESI and crystallographic data in CIF or other electronic format see DOI
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  publication-title: Stereochemistry of Organic Compounds
  doi: Eliel Wilen Mander
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Title 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
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