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Bae, Han Yong
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Direct Catalytic Asymmetric Mannich Reaction with Dithiomalonates as Excellent Mannich Donors: Organocatalytic Synthesis of (R)-Sitagliptin

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Title
Direct Catalytic Asymmetric Mannich Reaction with Dithiomalonates as Excellent Mannich Donors: Organocatalytic Synthesis of (R)-Sitagliptin
Author
Bae, Han YongKim, Mun JongSim, Jae HunSong, Choong Eui
Issue Date
201608
Publisher
WILEY-V C H VERLAG GMBH
Citation
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.55, no.36, pp.10825 - 10829
Abstract
In this study, dithiomalonates (DTMs) were demonstrated to be exceptionally efficient Mannich donors in terms of reactivity and stereoselectivity in cinchona-based-squaramide-catalyzed enantioselective Mannich reactions of diverse imines or -amidosulfones as imine surrogates. Owing to the superior reactivity of DTMs as compared to conventional malonates, the catalyst loading could be reduced to 0.1mol% without the erosion of enantioselectivity (up to 99%ee). Furthermore, by the use of a DTM, even some highly challenging primary alkyl -amidosulfones were smoothly converted into the desired adducts with excellent enantioselectivity (up to 97%ee), whereas the use of a malonate or monothiomalonate resulted in no reaction under identical conditions. The synthetic utility of the chiral Mannich adducts obtained from primary alkyl substrates was highlighted by the organocatalytic, coupling-reagent-free synthesis of the antidiabetic drug (-)-(R)-sitagliptin.
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DOI
http://dx.doi.org/10.1002/anie.201605167
ISSN
1433-7851
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