Abstract
The first, catalytic, enantioselective α-additions of isocyanides to aldehydes have been demonstrated (Passerini-type reactions). The catalytic system of silicon tetrachloride and a chiral bisphosphoramide 5a provided high yields and good to excellent enantioselectivities for the addition of tert-butyl isocyanide to a wide range of aldehydes (aromatic, olefinic, acetylenic, aliphatic). Aqueous workup afforded the α-hydroxy tert-butyl amides, whereas methanolic quench followed by basic workup afforded the ∞-hydroxy methyl esters.
Original language | English (US) |
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Pages (from-to) | 7825-7827 |
Number of pages | 3 |
Journal | Journal of the American Chemical Society |
Volume | 125 |
Issue number | 26 |
DOIs | |
State | Published - Jul 2 2003 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry