Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts

The diastereodivergent synthesis of bridged 1,2,3,4‐tetrahydroisoquinoline derivatives has been achieved by using appropriate modularly designed organocatalysts (MDOs) that are self‐assembled in situ from amino acids and cinchona alkaloid derivatives. The domino Mannich/aza‐Michael/aldol reaction be...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-06, Vol.362 (12), p.2419-2426
Main Authors: Jakkampudi, Satish, Konda, Swapna, Arman, Hadi, Zhao, John C.‐G.
Format: Article
Language:English
Subjects:
Acetates
Aldehydes
Amino acids
Aromatic compounds
Chemical synthesis
Derivatives
diastereodivergent synthesis
enantioselectivity
Modular design
organocatalysis
self-assembly
tetrahydroisoquinoline
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Summary:The diastereodivergent synthesis of bridged 1,2,3,4‐tetrahydroisoquinoline derivatives has been achieved by using appropriate modularly designed organocatalysts (MDOs) that are self‐assembled in situ from amino acids and cinchona alkaloid derivatives. The domino Mannich/aza‐Michael/aldol reaction between (E)‐2‐[2‐(3‐aryl‐3‐oxoprop‐1‐en‐1‐yl)phenyl]acetaldehydes and ethyl or benzyl (E)‐2‐[(4‐methoxyphenyl)imino]acetates catalyzed by MDOs gives two different diastereomers of the desired bridged tetrahydroisoquinolines in good yields and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to >99% ee). The diastereodivergence was achieved in the aldol reaction step.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000227