N-thioacylation of β-amino alcohols by N-(thioacyl)phthalimides: A facile synthesis of α-amine acid thiazolines

Christopher T. Brain; Allan Hallett; Soo Y. Ko

doi:10.1016/S0040-4039(97)10467-1

N-thioacylation of β-amino alcohols by N-(thioacyl)phthalimides: A facile synthesis of α-amine acid thiazolines

Christopher T. Brain
, Allan Hallett
, Soo Y. Ko

Department of Chemistry & Nanoscience

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

24 Scopus citations

Abstract

β-amino alcohols are selectively N-thioacylated by N- (thioacyl)phthalimides under very mild conditions to provide N- (hydroxyethyl)thioamides in high yields. Cyclodehydration with Burgess reagent then provides α-amino acid thiazolines. This approach provides a convenient alternative to those based upon thionation of a preformed N- (hydroxyethyl)amide.

Original language	English
Pages (from-to)	127-130
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	1-2
DOIs	https://doi.org/10.1016/S0040-4039(97)10467-1
State	Published - 1 Jan 1998

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title = "N-thioacylation of β-amino alcohols by N-(thioacyl)phthalimides: A facile synthesis of α-amine acid thiazolines",

abstract = "β-amino alcohols are selectively N-thioacylated by N- (thioacyl)phthalimides under very mild conditions to provide N- (hydroxyethyl)thioamides in high yields. Cyclodehydration with Burgess reagent then provides α-amino acid thiazolines. This approach provides a convenient alternative to those based upon thionation of a preformed N- (hydroxyethyl)amide.",

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T1 - N-thioacylation of β-amino alcohols by N-(thioacyl)phthalimides

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AU - Brain, Christopher T.

AU - Hallett, Allan

AU - Ko, Soo Y.

PY - 1998/1/1

Y1 - 1998/1/1

N2 - β-amino alcohols are selectively N-thioacylated by N- (thioacyl)phthalimides under very mild conditions to provide N- (hydroxyethyl)thioamides in high yields. Cyclodehydration with Burgess reagent then provides α-amino acid thiazolines. This approach provides a convenient alternative to those based upon thionation of a preformed N- (hydroxyethyl)amide.

AB - β-amino alcohols are selectively N-thioacylated by N- (thioacyl)phthalimides under very mild conditions to provide N- (hydroxyethyl)thioamides in high yields. Cyclodehydration with Burgess reagent then provides α-amino acid thiazolines. This approach provides a convenient alternative to those based upon thionation of a preformed N- (hydroxyethyl)amide.

UR - https://www.scopus.com/pages/publications/0031983552

U2 - 10.1016/S0040-4039(97)10467-1

DO - 10.1016/S0040-4039(97)10467-1

M3 - Article

AN - SCOPUS:0031983552

SN - 0040-4039

VL - 39

SP - 127

EP - 130

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1-2

ER -

N-thioacylation of β-amino alcohols by N-(thioacyl)phthalimides: A facile synthesis of α-amine acid thiazolines

Abstract

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