Modular Monodentate Oxaphospholane Ligands: Utility in Highly Efficient and Enantioselective 1,4-Diboration of 1,3-Dienes

Tune it up! Tunable, chiral, monodentate oxaphospholane ligands (termed OxaPhos) are highly effective in the Pt‐catalyzed title reaction, providing the 1,4‐addition products in enantiomer ratios approaching 99:1 (see scheme). In the presence of enantiomerically pure cis‐iBu‐OxaPhos, a catalyst loadi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-08, Vol.50 (34), p.7906-7909
Main Authors: Schuster, Christopher H., Li, Bo, Morken, James P.
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
asymmetric catalysis
boron
Boron Compounds - chemistry
ligand design
Ligands
Models, Molecular
Molecular Structure
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
oxidation
Stereoisomerism
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Summary:Tune it up! Tunable, chiral, monodentate oxaphospholane ligands (termed OxaPhos) are highly effective in the Pt‐catalyzed title reaction, providing the 1,4‐addition products in enantiomer ratios approaching 99:1 (see scheme). In the presence of enantiomerically pure cis‐iBu‐OxaPhos, a catalyst loading of only 0.02 mol % [Pt(dba)3] was sufficient for effective reaction. pin=pinacolato, dba=dibenzylideneacetone.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201102404