A bidirectional synthesis of spiroacetals via Rh(II)-catalysed C-H insertion

Acyclicmethylene acetals bearing two diazoester subunits have been converted to [5,5]-spiroacetals VIA bidirectional C-H insertion under Rh(II) catalysis. Using a chiral Rh(II) catalyst, the major diastereomer can be produced in high enantiomeric excess (89%).

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 53; no. 30; pp. 4219 - 4221
Main Authors Lepage, Romain J., White, Jonathan M., Coster, Mark J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 11.04.2017
Subjects
Acetals
Bearing
Bidirectional
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Insertion
Methylene
Physical Sciences
Science & Technology
Synthesis
MECHANISM
CONSTRUCTION
ANOMALOUS PRODUCTS
REACTIVITY
CHEMISTRY
CATALYST
RHODIUM CARBENOIDS
SPIROKETALS
STRATEGIES
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Summary:Acyclicmethylene acetals bearing two diazoester subunits have been converted to [5,5]-spiroacetals VIA bidirectional C-H insertion under Rh(II) catalysis. Using a chiral Rh(II) catalyst, the major diastereomer can be produced in high enantiomeric excess (89%).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc00459a