A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

James C. Barrow; Phung L. Ngo; Janetta M. Pellicore; Harold G. Selnick; Philippe G. Nantermet

doi:10.1016/S0040-4039(01)00122-8

A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

James C. Barrow, Phung L. Ngo, Janetta M. Pellicore, Harold G. Selnick, Philippe G. Nantermet

Research output: Contribution to journal › Article › peer-review

78 Scopus citations

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)
Pages (from-to)	2051-2054
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(01)00122-8
State	Published - Mar 11 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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T1 - A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

AU - Barrow, James C.

AU - Ngo, Phung L.

AU - Pellicore, Janetta M.

AU - Selnick, Harold G.

AU - Nantermet, Philippe G.

PY - 2001/3/11

Y1 - 2001/3/11

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4039(01)00122-8

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SP - 2051

EP - 2054

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

Abstract

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