Stereoselective bidirectional synthesis of spiroacetals via Rh(II)-catalysed double C–H insertion

The stereoselective synthesis of 5,5-spiroacetals by Rh(II)-catalysed double C–H insertion of methylene acetals bearing two diazo ester substituents is described. The diastereoselectivity of this bidirectional approach can be tuned through appropriate choice of catalyst, and chiral catalysts lead to...

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Bibliographic Details
Published inTetrahedron Vol. 74; no. 12; pp. 1313 - 1321
Main Authors Lepage, Romain J., Coster, Mark J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.03.2018
Elsevier
Subjects
Bidirectional
Chemistry
Chemistry, Organic
C–H insertion
Physical Sciences
Rh(II)-catalysis
Science & Technology
Spiroacetal
Stereoselectivity
Stereoselectivity
Rh(II)-catalysis
Bidirectional
C–H insertion
Spiroacetal
PERFORMANCE
CATALYST
KINETIC SPIROCYCLIZATION
MARINE NATURAL-PRODUCTS
SPIROKETALS
AMINATION
GLYCAL EPOXIDES
C-H insertion
CHEMISTRY
RHODIUM CARBENOIDS
STEREOCONTROLLED SYNTHESIS
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Summary:The stereoselective synthesis of 5,5-spiroacetals by Rh(II)-catalysed double C–H insertion of methylene acetals bearing two diazo ester substituents is described. The diastereoselectivity of this bidirectional approach can be tuned through appropriate choice of catalyst, and chiral catalysts lead to products with up to 89% ee. The diastereoselectivity of the first cyclisation suggests that the second cyclisation proceeds via a non-concerted pathway. [Display omitted]
Bibliography:Australian Research Council
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.01.043