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- W3013930599 abstract "A method for catalytic regio- and enantioselective synthesis of trifluoromethyl-substituted and aryl-, heteroaryl-, alkenyl-, and alkynyl-substituted homoallylic α-tertiary NH2 -amines is introduced. Easy-to-synthesize and robust N-silyl ketimines are converted to NH-ketimines in situ, which then react with a Z-allyl boronate. Transformations are promoted by a readily accessible l-threonine-derived aminophenol-based boryl catalyst, affording the desired products in up to 91 % yield, >98:2 α:γ selectivity, >98:2 Z:E selectivity, and >99:1 enantiomeric ratio. A commercially available aminophenol may be used, and allyl boronates, which may contain an alkyl-, a chloro-, or a bromo-substituted Z-alkene, can either be purchased or prepared by catalytic stereoretentive cross-metathesis. What is more, Z-trisubstituted allyl boronates may be used. Various chemo-, regio-, and diastereoselective transformations of the α-tertiary homoallylic NH2 -amine products highlight the utility of the approach; this includes diastereo- and regioselective epoxide formation/trichloroacetic acid cleavage to generate differentiated diol derivatives." @default.
- W3013930599 created "2020-04-03" @default.
- W3013930599 creator A5051513258 @default.
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- W3013930599 date "2020-05-08" @default.
- W3013930599 modified "2023-09-25" @default.
- W3013930599 title "Regio‐ and Enantioselective Synthesis of Trifluoromethyl‐Substituted Homoallylic α‐Tertiary NH <sub>2</sub> ‐Amines by Reactions Facilitated by a Threonine‐Based Boron‐Containing Catalyst" @default.
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- W3013930599 doi "https://doi.org/10.1002/anie.202001184" @default.
- W3013930599 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7454190" @default.
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