Enantioselective preparation of a stable boronate complex stereogenic only at boron

Journal of the American Chemical Society

Volumn 130, Issue 49, 2008, Pages 16450-16451

  Kaiser, Peter F ^a   White, Jonathan M ^a   Hutton, Craig A ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; BORONIC ACID DERIVATIVE; ORGANOBORON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

BORON; BORONIC ACIDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 57549108655     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8044629     Document Type: Article

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36. A further possibility suggested by a reviewer is that 3 exists as a single atropisomer (about the naphthyl-methine carbon bond) and that, upon isomerization to 4, the atropisomer does not undergo rotation either to the opposite atropisomer or to bring the C=N bond into planarity with the naphthyl group, prior to coordination to phenylboronic acid.