Unexpected 1,3-oxazolidine formation in the attempted oxidation of N-Aryl-N-Methyl substituted b(beta)-amino alcohols using pyridium dichromate

Jari Yli-Kauhaluoma, Curtis Harwig, Paul Wentworth, Kim Janda (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

23 Citations (Scopus)

Abstract

1,3-Oxazolidines were obtained from the reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane. A single electron transfer mechanism, SET, is proposed to account for the formation of the 1,3-oxazolidines.

A general approach to 1,3-oxazolidines is reported from a novel reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane.
Original languageEnglish
Pages (from-to)2269-2272
JournalTetrahedron Letters
Volume39
Issue number16
DOIs
Publication statusPublished - 1998
MoE publication typeA1 Journal article-refereed

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Phenazopyridine
Amino Alcohols
Methylene Chloride
Oxidation
Electrons
oxazolidine
pyridinium dichromate

Cite this

Yli-Kauhaluoma, Jari ; Harwig, Curtis ; Wentworth, Paul ; Janda, Kim. / Unexpected 1,3-oxazolidine formation in the attempted oxidation of N-Aryl-N-Methyl substituted b(beta)-amino alcohols using pyridium dichromate. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 16. pp. 2269-2272.
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abstract = "1,3-Oxazolidines were obtained from the reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane. A single electron transfer mechanism, SET, is proposed to account for the formation of the 1,3-oxazolidines.A general approach to 1,3-oxazolidines is reported from a novel reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane.",
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Unexpected 1,3-oxazolidine formation in the attempted oxidation of N-Aryl-N-Methyl substituted b(beta)-amino alcohols using pyridium dichromate. / Yli-Kauhaluoma, Jari; Harwig, Curtis; Wentworth, Paul; Janda, Kim (Corresponding Author).

In: Tetrahedron Letters, Vol. 39, No. 16, 1998, p. 2269-2272.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Unexpected 1,3-oxazolidine formation in the attempted oxidation of N-Aryl-N-Methyl substituted b(beta)-amino alcohols using pyridium dichromate

AU - Yli-Kauhaluoma, Jari

AU - Harwig, Curtis

AU - Wentworth, Paul

AU - Janda, Kim

PY - 1998

Y1 - 1998

N2 - 1,3-Oxazolidines were obtained from the reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane. A single electron transfer mechanism, SET, is proposed to account for the formation of the 1,3-oxazolidines.A general approach to 1,3-oxazolidines is reported from a novel reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane.

AB - 1,3-Oxazolidines were obtained from the reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane. A single electron transfer mechanism, SET, is proposed to account for the formation of the 1,3-oxazolidines.A general approach to 1,3-oxazolidines is reported from a novel reaction of N-methyl substituted β-amino alcohols with pyridinium dichromate in dichloromethane.

U2 - 10.1016/S0040-4039(98)00289-5

DO - 10.1016/S0040-4039(98)00289-5

M3 - Article

VL - 39

SP - 2269

EP - 2272

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 16

ER -