A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide
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 tha...
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| Published in: | Tetrahedron letters Vol. 42; no. 11; pp. 2051 - 2054 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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11-03-2001
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| 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.
Graphic |
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| AbstractList | 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.
Graphic |
| Author | Nantermet, Philippe G Barrow, James C Ngo, Phung L Pellicore, Janetta M Selnick, Harold G |
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tert-butylsulfinimines derived from
tert-butyldimethylsiloxyacetaldehyde stereoselectively generates protected 1,2-amino... |
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| Title | A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide |
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