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Catalytic Enantioselective Addition of Pyrazol‐5‐ones to Trisubstituted Nitroalkenes with an N ‐Sulfinylurea Organocatalyst
Author(s) -
Phelan James P.,
Ellman Jonathan A.
Publication year - 2016
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.201600110
Subject(s) - enantioselective synthesis , chemistry , nitroalkene , nucleophile , oxetane , michael reaction , squaramide , organic chemistry , nitronate , epoxide , catalysis , organocatalysis , yield (engineering) , enantiomeric excess , nitro , alkyl , materials science , metallurgy
The first example of enantioselective nitronate protonation following Michael addition of a carbon nucleophile to an α,β,β‐trisubstituted nitroalkene is reported. An N ‐sulfinylurea catalyst was employed to catalyze the addition of a variety of 3‐substituted pyrazol‐5‐one nucleophiles to trisubstituted nitroalkenes incorporating an oxetane or azetidine ring at the β‐position. The nitroalkane‐pyrazolone adducts were obtained with good yield and enantioselectivity. Furthermore, the Michael addition products can be reduced to the corresponding enantioenriched amines with minimal loss of enantiomeric purity.