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Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts
Author(s) -
Jakkampudi Satish,
Konda Swapna,
Arman Hadi,
Zhao John C.G.
Publication year - 2020
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.202000227
Subject(s) - chemistry , aldol reaction , tetrahydroisoquinoline , domino , organocatalysis , diastereomer , catalysis , cinchona , enantioselective synthesis , aryl , mannich reaction , organic chemistry , combinatorial chemistry , alkyl
Abstract 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.