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- Title
Catalytic Asymmetric Mannich-Type Reaction of N-Alkylidene-α-Aminoacetonitrile with Ketimines.
- Authors
Lin, Shaoquan; Kawato, Yuji; Kumagai, Naoya; Shibasaki, Masakatsu
- Abstract
Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Brønsted base cooperative catalyst allows for an efficient stereoselective coupling of N-alkylidene-α-aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra- and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol % catalyst loading.
- Subjects
MANNICH reaction; IMINES; ALKYLIDENES; LEWIS acids; AMINOACETONITRILE; ORGANIC synthesis
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 17, p5272
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201412377