Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines

C.R. Alonso-Cruz, A.R. Kennedy, M.S. Rodriguez, E. Suarez

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the D-gluco, D-galacto, D-lacto, and L-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These -iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These -iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.
Original languageEnglish
Pages (from-to)3729-3732
Number of pages3
JournalOrganic Letters
Volume5
Issue number20
DOIs
Publication statusPublished - 4 Sep 2003

Fingerprint

Azirines
Azides
carbohydrates
fragmentation
Carbohydrates
synthesis
iodine
Sugar Alcohols
benzene
Benzene
Iodine
preparation
Large scale systems
carbon
Carbon
Hot Temperature
alkoxyl radical

Keywords

  • reaction of 3-azido-2
  • 3-dideoxy-hexopyranose compounds
  • D-gluco
  • D-galacto
  • D-lacto
  • L-arabino
  • carbohydrate
  • benzene
  • iodine
  • dehydroiodination
  • heterocyclic systems

Cite this

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title = "Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral {\ss}-iodo azides, vinyl azides and 2H-azirines",
abstract = "The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the D-gluco, D-galacto, D-lacto, and L-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These -iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These -iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.",
keywords = "reaction of 3-azido-2, 3-dideoxy-hexopyranose compounds, D-gluco, D-galacto, D-lacto, L-arabino, carbohydrate, benzene, iodine, dehydroiodination, heterocyclic systems",
author = "C.R. Alonso-Cruz and A.R. Kennedy and M.S. Rodriguez and E. Suarez",
year = "2003",
month = "9",
day = "4",
doi = "10.1021/ol035435g",
language = "English",
volume = "5",
pages = "3729--3732",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
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Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines. / Alonso-Cruz, C.R.; Kennedy, A.R.; Rodriguez, M.S.; Suarez, E.

In: Organic Letters, Vol. 5, No. 20, 04.09.2003, p. 3729-3732.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines

AU - Alonso-Cruz, C.R.

AU - Kennedy, A.R.

AU - Rodriguez, M.S.

AU - Suarez, E.

PY - 2003/9/4

Y1 - 2003/9/4

N2 - The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the D-gluco, D-galacto, D-lacto, and L-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These -iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These -iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.

AB - The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the D-gluco, D-galacto, D-lacto, and L-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These -iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These -iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.

KW - reaction of 3-azido-2

KW - 3-dideoxy-hexopyranose compounds

KW - D-gluco

KW - D-galacto

KW - D-lacto

KW - L-arabino

KW - carbohydrate

KW - benzene

KW - iodine

KW - dehydroiodination

KW - heterocyclic systems

UR - http://pubs.acs.org/cgi-bin/article.cgi/orlef7/2003/5/i20/html/ol035435g.html

UR - http://dx.doi.org/10.1021/ol035435g

U2 - 10.1021/ol035435g

DO - 10.1021/ol035435g

M3 - Article

VL - 5

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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ER -