Beilstein J. Org. Chem.2020,16, 2671–2678, doi:10.3762/bjoc.16.217
, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain 10.3762/bjoc.16.217 Abstract In the present work, arylethynes were studied as new C-nucleophiles in the asymmetric Mannich addition reactions with (S
afford diastereomerically pure compounds. The purified Mannich addition products were deprotected to give the target enantiomerically pure trifluoromethylpropargylamines. A mechanistic rationale for the observed stereochemical outcome is discussed.
Keywords: arylethynes; asymmetric Mannich reaction; C
optimized reaction conditions in hand, we examined the generality of these asymmetric Mannich reactions by using various arylethynes 2 (Scheme 2). Under standard reaction conditions, all the tested substrates worked well to generate the corresponding Mannich adducts in moderate to good yields. In particular
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Graphical Abstract
Figure 1:
Anti-HIV compound containing a trifluoromethylpropargylamine moiety.