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Diastereodivergent Catalysis Using Modularly Designed Organocatalysts: Synthesis of both cis ‐ and trans ‐Fused Pyrano[2,3‐ b ]pyrans
Author(s) -
Huang Huicai,
Konda Swapna,
Zhao John C.G.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201510134
Subject(s) - cinchona , thiourea , pyran , chemistry , enantiomer , ring (chemistry) , organocatalysis , catalysis , tandem , enantioselective synthesis , stereochemistry , combinatorial chemistry , organic chemistry , materials science , composite material
Both enantiomers of cis ‐ and trans ‐fused 3,4,4a,8a‐tetrahydro‐2H,5H‐pyrano[2,3‐b]pyran‐7‐carboxylates have been obtained in high diastereoselectivities and enantioselectivities from the same starting materials using a tandem inverse‐electron‐demand hetero‐Diels–Alder/oxa‐Michael reaction catalyzed by modularly designed organocatalysts (MDOs). Diastereodivergence was achieved in these reactions through the direct control of the stereochemistry of the bridgehead atoms of the fused ring using new MDOs self‐assembled from both enantiomers of proline and cinchona alkaloid thiourea derivatives.