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Enantioselective synthesis of spiro[4 H -pyran-3,3′-oxindole] derivatives catalyzed by cinchona alkaloid thioureas: Significant water effects on the enantioselectivity

https://doi.org/10.1080/00397911.2019.1651866

Konda, Swapna; Jakkampudi, Satish; Arman, Hadi D.; Zhao, John C.-G. (August 2019, Synthetic Communications)

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Enantioselective anti-Mannich reaction catalyzed by modularly designed organocatalysts

https://doi.org/10.1016/j.tet.2018.09.006

Konda, Swapna; Zhao, John C.-G. (October 2018, Tetrahedron)

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Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts

https://doi.org/10.1002/adsc.202000227

Jakkampudi, Satish; Konda, Swapna; Arman, Hadi; Zhao, John_C‐G (April 2020, Advanced Synthesis & Catalysis)

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. magnified image
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