Stereoselective Synthesis of 3‐Oxabicyclo[3.3.1]Nonan‐2‐Ones via a Domino Reaction Catalyzed by Modularly Designed Organocatalysts

A highly stereoselective method for the synthesis of functionalized 3‐oxabicyclo[3.3.1]nonan‐2‐one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Michael‐hemiacetalization‐Michael reaction of (E)...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-01, Vol.361 (1), p.208-213
Main Authors: Parella, Ramarao, Jakkampudi, Satish, Arman, Hadi, Zhao, John C.‐G.
Format: Article
Language:English
Subjects:
asymmetric
domino reaction
hemiacetalization
Michael reaction
modularly designed organocatalyst
organocatalysis
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Summary:A highly stereoselective method for the synthesis of functionalized 3‐oxabicyclo[3.3.1]nonan‐2‐one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Michael‐hemiacetalization‐Michael reaction of (E)‐3‐aryl‐2‐nitroprop‐2‐enols and (E)‐7‐aryl‐7‐oxohept‐5‐enals followed by a PCC oxidation. Using the modularly designed organocatalysts (MDOs) self‐assembled from cinchona alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good yields (up to 84%), excellent diastereoselectivities (≥99:1 dr), and high enantioselectivities (up to 96% ee).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800987