Remote Sulfonamido Group Enhances Reactivity and Selectivity for Asymmetric Michael Addition of Nitroalkanes to α,β-Unsaturated Aldehydes

The pyrrolidine–camphorsulfonamide‐based catalyst 1 a catalyzes the enantioselective conjugate addition of nitroalkanes to α,β‐unsaturated aldehydes in the presence of five equivalents of water in iPrOH to give the corresponding chiral Michael adducts in good yields and high enantioselectivities (up...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2014-09, Vol.9 (9), p.2444-2448
Main Authors: Huang, Yu-Chao, Uang, Biing-Jiun
Format: Article
Language:English
Subjects:
asymmetric synthesis
michael addition
nitroalkane
organocatalysis
α,β‐unsaturated aldehyde
β-unsaturated aldehyde
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Summary:The pyrrolidine–camphorsulfonamide‐based catalyst 1 a catalyzes the enantioselective conjugate addition of nitroalkanes to α,β‐unsaturated aldehydes in the presence of five equivalents of water in iPrOH to give the corresponding chiral Michael adducts in good yields and high enantioselectivities (up to 99 % ee) with a catalyst loading as low as 1 mol %. Two birds with one stone: The pyrrolidine–camphorsulfonamide‐based catalyst 1 a catalyzes the enantioselective conjugate addition of nitroalkanes to α,β‐unsaturated aldehydes in the presence of 5 equivalents of water in iPrOH to give the corresponding chiral Michael adducts in good yields and high enantioselectivities (up to 99 % ee) with catalyst loading as low as 1 mol %.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201402516