Chiral cyclobutanols and cyclopentane dimers via samarium(II) iodide induced keto-olefin cyclisations of carbohydrate-derived unsaturated ketones

D. Bradley G. Williams; Judy Caddy; Kevin Blann; J. J.Cronjé Grové; Cedric W. Holzapfel

doi:10.1055/s-0029-1216824

Chiral cyclobutanols and cyclopentane dimers via samarium(II) iodide induced keto-olefin cyclisations of carbohydrate-derived unsaturated ketones

D. Bradley G. Williams, Judy Caddy, Kevin Blann, J. J.Cronjé Grové, Cedric W. Holzapfel

Chemical Sciences

University of Johannesburg

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

8 Citations (Scopus)

Abstract

Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI₂. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.

Original language	English
Article number	P02909SS
Pages (from-to)	2009-2014
Number of pages	6
Journal	Synthesis
Issue number	12
DOIs	https://doi.org/10.1055/s-0029-1216824
Publication status	Published - Jun 2009

Keywords

Carbocycles
Carbohydrates
Radical reactions
Ring closure
Samarium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0029-1216824

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title = "Chiral cyclobutanols and cyclopentane dimers via samarium(II) iodide induced keto-olefin cyclisations of carbohydrate-derived unsaturated ketones",

abstract = "Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.",

keywords = "Carbocycles, Carbohydrates, Radical reactions, Ring closure, Samarium",

author = "Williams, \{D. Bradley G.\} and Judy Caddy and Kevin Blann and Grov{\'e}, \{J. J.Cronj{\'e}\} and Holzapfel, \{Cedric W.\}",

year = "2009",

month = jun,

doi = "10.1055/s-0029-1216824",

language = "English",

pages = "2009--2014",

journal = "Synthesis",

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publisher = "Georg Thieme Verlag",

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T1 - Chiral cyclobutanols and cyclopentane dimers via samarium(II) iodide induced keto-olefin cyclisations of carbohydrate-derived unsaturated ketones

AU - Williams, D. Bradley G.

AU - Caddy, Judy

AU - Blann, Kevin

AU - Grové, J. J.Cronjé

AU - Holzapfel, Cedric W.

PY - 2009/6

Y1 - 2009/6

N2 - Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.

AB - Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.

KW - Carbocycles

KW - Carbohydrates

KW - Radical reactions

KW - Ring closure

KW - Samarium

UR - https://www.scopus.com/pages/publications/67650094915

U2 - 10.1055/s-0029-1216824

DO - 10.1055/s-0029-1216824

M3 - Article

AN - SCOPUS:67650094915

SN - 0039-7881

SP - 2009

EP - 2014

JO - Synthesis

JF - Synthesis

IS - 12

M1 - P02909SS

ER -

Chiral cyclobutanols and cyclopentane dimers via samarium(II) iodide induced keto-olefin cyclisations of carbohydrate-derived unsaturated ketones

Abstract

Keywords

ASJC Scopus subject areas

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