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- Title
Enantioselective Radical Alkynylation of C(sp<sup>3</sup>)-H Bonds Using Sulfoximine as a Traceless Chiral Auxiliary.
- Authors
Nagatomo, Masanori; Yoshioka, Shun; Inoue, Masayuki
- Abstract
Enantioselective alkynylation of C(sp3)-H bonds adjacent to a nitrogen atom has been achieved using only chiral p-tolyl tert-butyldimethylsilylethynyl sulfoximine and benzophenone under photo-irradiation conditions. A twocarbon alkyne unit was chemo- and enantioselectively transferred at the nitrogen-substituted methylene to produce the optically active propargylic amines of various structures. Remarkably, the NH-unprotected sulfoximine group efficiently transmits its stereochemical information to the product and functions as a traceless chiral auxiliary.
- Subjects
ENANTIOSELECTIVE catalysis; CARBON-hydrogen bonds; SULFOXIMINES; ALKYNE synthesis; CHIRALITY of nuclear particles; BENZOPHENONES
- Publication
Chemistry - An Asian Journal, 2015, Vol 10, Issue 1, p120
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201402983