Abstract
Addition of organometallic reagents to tert-butylsulfinimines derived from tert-butyldimethylsiloxyacetaldehyde stereoselectively generates protected 1,2-amino alcohols. Removal of the acid labile protecting groups affords amino alcohols in high yield. The predominant diastereomer is opposite to that predicted by the traditional Ellman model; therefore, a chelation model invoking rapid E/Z isomerization of the imine is proposed to rationalize the observed selectivity.
Original language | English (US) |
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Pages (from-to) | 2051-2054 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 42 |
Issue number | 11 |
DOIs | |
State | Published - Mar 11 2001 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry