Phosphate-Tether-Mediated Ring-Closing Metathesis for the Preparation of Complex 1,3-anti-Diol-Containing Subunits

An array of examples of diastereoselective, phosphate‐tether‐mediated ring‐closing metathesis reactions, which highlight the importance of product ring size and substrate stereochemical compatibility, as well as complexity, is reported. Studies focus primarily on the formation of bicyclo[n.3.1]phosp...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-06, Vol.19 (25), p.8088-8093
Main Authors: Chegondi, Rambabu, Maitra, Soma, Markley, Jana L., Hanson, Paul R.
Format: Article
Language:English
Subjects:
Alcohols
Arrays
bicyclic phosphate
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Chemistry
Compatibility
Complexity
Decomposition reactions
diastereotopic differentiation
Joining
Mediation
Metathesis
Models, Molecular
Molecular Structure
natural products
phosphate tether
Phosphates - chemistry
ring-closing metathesis
Stereoisomerism
Studies
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Summary:An array of examples of diastereoselective, phosphate‐tether‐mediated ring‐closing metathesis reactions, which highlight the importance of product ring size and substrate stereochemical compatibility, as well as complexity, is reported. Studies focus primarily on the formation of bicyclo[n.3.1]phosphates, involving the coupling of C2‐symmetric dienediol subunits with a variety of simple, as well as complex, alcohol partners. Phosphate‐tether mediation: An array of examples of diastereoselective, phosphate‐tether‐mediated ring‐closing metathesis reactions, which highlight the importance of product ring size and substrate stereochemical complexity, is reported (see scheme). Bicyclo[n.3.1]phosphates can be prepared utilizing the tripodal coupling of C2‐symmetric dienediol subunits with a variety of simple, as well as complex alcohol partners.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201300913