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Stereoselective Synthesis of 3‐Oxabicyclo[3.3.1]Nonan‐2‐Ones via a Domino Reaction Catalyzed by Modularly Designed Organocatalysts
Author(s) -
Parella Ramarao,
Jakkampudi Satish,
Arman Hadi,
Zhao John C.G.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800987
Subject(s) - stereocenter , chemistry , domino , stereoselectivity , cinchona , aryl , organocatalysis , cascade reaction , catalysis , michael reaction , combinatorial chemistry , organic chemistry , enantioselective synthesis , stereochemistry , alkyl
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 ).