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Diastereodivergent Synthesis of Hexahydro‐6 H ‐benzo[ c ]chromen‐6‐one Derivatives Catalyzed by Modularly Designed Organocatalysts
Author(s) -
Jakkampudi Satish,
Parella Ramarao,
Arman Hadi D.,
Zhao John C.G.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806447
Subject(s) - catalysis , chemistry , combinatorial chemistry , organic chemistry
The diastereodivergent synthesis of hexahydro‐6 H ‐benzo[ c ]chromen‐6‐one derivatives with good to high diastereoselectivities (up to 98:2 d.r.) and enantioselectivities (up to >99 % ee ) has been achieved by using a domino Michael/Michael/hemiacetalization reaction between trans ‐2‐hydroxy‐β‐nitrostyrenes and trans ‐7‐oxo‐5‐heptenals followed by oxidation. With use of appropriate modularly designed organocatalysts (MDOs) that are self‐assembled in situ from amino acid derivatives and cinchona alkaloid derivatives, two different diastereomers of the desired hexahydro‐6 H ‐benzo[ c ]chromen‐6‐ones are obtained from the same substrates.