Literature DB >> 15004373

A 1,3,2-oxazaborolidine dimer derived from (S)-alpha,alpha-diphenylprolinol.

Margarita Ortiz-Marciales1, Melvin De Jesús, Eduvigis González, Raphael G Raptis, Peter Baran.   

Abstract

The reaction of (S)-alpha,alpha-diphenylprolinol with an excess of borane-tetrahydrofuran complex yields a stable crystalline material with the composition C34H38B2N2O2, which features a borane adduct of a spirocyclic structure with two oxazaborolidine rings joined by a central tetrahedral B atom. This dimeric oxazaborolidine complex, viz. 3,3,3',3'-tetraphenyl-1,1'-spirobi(3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole)-7-borane, is the dominant product under various reaction conditions; its crystal structure is consistent with 11B, 1H and 13C NMR and IR analyses.

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Year:  2004        PMID: 15004373      PMCID: PMC2814345          DOI: 10.1107/S0108270104000666

Source DB:  PubMed          Journal:  Acta Crystallogr C        ISSN: 0108-2701            Impact factor:   1.172


  2 in total

1.  Dimeric phenalenyl-based neutral radical molecular conductors.

Authors:  X Chi; M E Itkis; K Kirschbaum; A A Pinkerton; R T Oakley; A W Cordes; R C Haddon
Journal:  J Am Chem Soc       Date:  2001-05-02       Impact factor: 15.419

2.  Coordinative N-->B bond formation and hydrogen-bonded molecular ladders in 2,5-bis[(N-->B)-(2-aminoethoxy)phenylboryl]thiophene.

Authors:  Philip J Cox; James L Wardell
Journal:  Acta Crystallogr C       Date:  2002-07-31       Impact factor: 1.172

  2 in total
  3 in total

1.  SYNTHESIS OF SPIROBORATE ESTERS FROM 1,2-AMINOALCOHOLS, ETHYLENE GLYCOL AND TRIISOPROPYL BORATE: PREPARATION OF (S)-1-(1,3,2-DIOXABOROLAN-2-YLOXY)-3-METHYL-1,1-DIPHENYLBUTAN-2-AMINE.

Authors:  Viatcheslav Stepanenko; Kun Huang; Margarita Ortiz-Marciales; David Hughes
Journal:  Organic Synth       Date:  2010

2.  Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.

Authors:  Kun Huang; Francisco G Merced; Margarita Ortiz-Marciales; Héctor J Meléndez; Wildeliz Correa; Melvin De Jesús
Journal:  J Org Chem       Date:  2008-05-01       Impact factor: 4.354

3.  Spiroborate ester-mediated asymmetric synthesis of beta-hydroxy ethers and its conversion to highly enantiopure beta-amino ethers.

Authors:  Kun Huang; Margarita Ortiz-Marciales; Wildeliz Correa; Edgardo Pomales; Xaira Y López
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354

  3 in total

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