Galactose-Imines in the staudinger reaction

Gunda I. Georg; Eyüp Akgün; Peter M. Mashava; Mark Milstead; He Ping; Zhi jun Wu; David Vander Velde; Fusao Takusagawa

doi:10.1016/0040-4039(92)88153-V

Galactose-Imines in the staudinger reaction

Gunda I. Georg, Eyüp Akgün, Peter M. Mashava, Mark Milstead, He Ping, Zhi jun Wu, David Vander Velde, Fusao Takusagawa

Medicinal Chemistry

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

33 Scopus citations

Abstract

Staudinger reaction of imines 1 and 2 derived from galactose with a variety of acid chlorides resulted in the formation of two β-lactams with cis configuration, typically in a 60:40 ratio and in good yields. The β-lactams were separated and the absolute stereochemistry of the diastereoisomers was determined by single crystal X-ray analysis and correlation of their ¹H-NMR data.

Original language	English (US)
Pages (from-to)	2111-2114
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	16
DOIs	https://doi.org/10.1016/0040-4039(92)88153-V
State	Published - Apr 14 1992

Bibliographical note

Funding Information:
Acknowledgements:F inanciala ssistancfer om theN ationalI nstituteso f Health (GM 42260a nd CA 52790), the Biomedical ResearchF und (RR 5606) at the University of Kansas, and the University of Zimbabwe ResearchB oardf or a travelg rantt o P. M. M. is acknowledged.

Keywords

Staudinger reaction
asymmetric synthesis
α-hydroxy-β-amino acids
β-lactams

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title = "Galactose-Imines in the staudinger reaction",

abstract = "Staudinger reaction of imines 1 and 2 derived from galactose with a variety of acid chlorides resulted in the formation of two β-lactams with cis configuration, typically in a 60:40 ratio and in good yields. The β-lactams were separated and the absolute stereochemistry of the diastereoisomers was determined by single crystal X-ray analysis and correlation of their 1H-NMR data.",

keywords = "Staudinger reaction, asymmetric synthesis, α-hydroxy-β-amino acids, β-lactams",

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note = "Funding Information: Acknowledgements:F inanciala ssistancfer om theN ationalI nstituteso f Health (GM 42260a nd CA 52790), the Biomedical ResearchF und (RR 5606) at the University of Kansas, and the University of Zimbabwe ResearchB oardf or a travelg rantt o P. M. M. is acknowledged.",

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doi = "10.1016/0040-4039(92)88153-V",

language = "English (US)",

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T1 - Galactose-Imines in the staudinger reaction

AU - Georg, Gunda I.

AU - Akgün, Eyüp

AU - Mashava, Peter M.

AU - Milstead, Mark

AU - Ping, He

AU - Wu, Zhi jun

AU - Velde, David Vander

AU - Takusagawa, Fusao

N1 - Funding Information: Acknowledgements:F inanciala ssistancfer om theN ationalI nstituteso f Health (GM 42260a nd CA 52790), the Biomedical ResearchF und (RR 5606) at the University of Kansas, and the University of Zimbabwe ResearchB oardf or a travelg rantt o P. M. M. is acknowledged.

PY - 1992/4/14

Y1 - 1992/4/14

N2 - Staudinger reaction of imines 1 and 2 derived from galactose with a variety of acid chlorides resulted in the formation of two β-lactams with cis configuration, typically in a 60:40 ratio and in good yields. The β-lactams were separated and the absolute stereochemistry of the diastereoisomers was determined by single crystal X-ray analysis and correlation of their 1H-NMR data.

AB - Staudinger reaction of imines 1 and 2 derived from galactose with a variety of acid chlorides resulted in the formation of two β-lactams with cis configuration, typically in a 60:40 ratio and in good yields. The β-lactams were separated and the absolute stereochemistry of the diastereoisomers was determined by single crystal X-ray analysis and correlation of their 1H-NMR data.

KW - Staudinger reaction

KW - asymmetric synthesis

KW - α-hydroxy-β-amino acids

KW - β-lactams

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 16

ER -

Galactose-Imines in the staudinger reaction

Abstract

Bibliographical note

Keywords

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