Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones

Petra Pádár; Attila Bokros; Gábor Paragi; Péter Forgó; Zoltán Kele; Nicola M. Howarth; Lajos Kovács

doi:10.1021/jo061503b

Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones

Petra Pádár, Attila Bokros, Gábor Paragi, Péter Forgó, Zoltán Kele, Nicola M. Howarth, Lajos Kovács

School of Engineering & Physical Sciences

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

23 Citations (Scopus)

Abstract

8-Benzyloxymethyl-3,4,5-tribenzoyloxy-9-oxa-1-azabicyclo[4.2.1]nonane has been prepared as the single diastereoisomer 8 from an intramolecular 1,3-dipolar cycloaddition involving 2-(benzyloxy)acetaldehyde and ?-unsaturated hydroxylamine 7 derived from methyl a-D-glucopyranoside. The analogous 8-methoxycarbonyl 9-oxa-1-azabicyclo[4.2.1]nonane was afforded in a similar manner, from methyl D-galactopyranoside and methyl glyoxylate, as a 3:1 mixture of diastereoisomers 15 and 16. When conducted in achiral ionic liquid 17 this ratio increased to 8:1, and in chiral ionic liquid 18, compound 15 was formed exclusively. © 2006 American Chemical Society.

Original language	English
Pages (from-to)	8669-8672
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	71
Issue number	22
DOIs	https://doi.org/10.1021/jo061503b
Publication status	Published - 27 Oct 2006

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@article{10c54d90ad2b448e9e29eaca7b4ebc20,

title = "Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones",

abstract = "8-Benzyloxymethyl-3,4,5-tribenzoyloxy-9-oxa-1-azabicyclo[4.2.1]nonane has been prepared as the single diastereoisomer 8 from an intramolecular 1,3-dipolar cycloaddition involving 2-(benzyloxy)acetaldehyde and ?-unsaturated hydroxylamine 7 derived from methyl a-D-glucopyranoside. The analogous 8-methoxycarbonyl 9-oxa-1-azabicyclo[4.2.1]nonane was afforded in a similar manner, from methyl D-galactopyranoside and methyl glyoxylate, as a 3:1 mixture of diastereoisomers 15 and 16. When conducted in achiral ionic liquid 17 this ratio increased to 8:1, and in chiral ionic liquid 18, compound 15 was formed exclusively. {\textcopyright} 2006 American Chemical Society.",

author = "Petra P{\'a}d{\'a}r and Attila Bokros and G{\'a}bor Paragi and P{\'e}ter Forg{\'o} and Zolt{\'a}n Kele and Howarth, {Nicola M.} and Lajos Kov{\'a}cs",

year = "2006",

month = oct,

day = "27",

doi = "10.1021/jo061503b",

language = "English",

volume = "71",

pages = "8669--8672",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "22",

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TY - JOUR

T1 - Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones

AU - Pádár, Petra

AU - Bokros, Attila

AU - Paragi, Gábor

AU - Forgó, Péter

AU - Kele, Zoltán

AU - Howarth, Nicola M.

AU - Kovács, Lajos

PY - 2006/10/27

Y1 - 2006/10/27

N2 - 8-Benzyloxymethyl-3,4,5-tribenzoyloxy-9-oxa-1-azabicyclo[4.2.1]nonane has been prepared as the single diastereoisomer 8 from an intramolecular 1,3-dipolar cycloaddition involving 2-(benzyloxy)acetaldehyde and ?-unsaturated hydroxylamine 7 derived from methyl a-D-glucopyranoside. The analogous 8-methoxycarbonyl 9-oxa-1-azabicyclo[4.2.1]nonane was afforded in a similar manner, from methyl D-galactopyranoside and methyl glyoxylate, as a 3:1 mixture of diastereoisomers 15 and 16. When conducted in achiral ionic liquid 17 this ratio increased to 8:1, and in chiral ionic liquid 18, compound 15 was formed exclusively. © 2006 American Chemical Society.

AB - 8-Benzyloxymethyl-3,4,5-tribenzoyloxy-9-oxa-1-azabicyclo[4.2.1]nonane has been prepared as the single diastereoisomer 8 from an intramolecular 1,3-dipolar cycloaddition involving 2-(benzyloxy)acetaldehyde and ?-unsaturated hydroxylamine 7 derived from methyl a-D-glucopyranoside. The analogous 8-methoxycarbonyl 9-oxa-1-azabicyclo[4.2.1]nonane was afforded in a similar manner, from methyl D-galactopyranoside and methyl glyoxylate, as a 3:1 mixture of diastereoisomers 15 and 16. When conducted in achiral ionic liquid 17 this ratio increased to 8:1, and in chiral ionic liquid 18, compound 15 was formed exclusively. © 2006 American Chemical Society.

U2 - 10.1021/jo061503b

DO - 10.1021/jo061503b

M3 - Article

SN - 0022-3263

VL - 71

SP - 8669

EP - 8672

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones

Abstract

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