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Further studies on silatropic carbonyl ene cyclisations: β-crotyl(diphenyl)silyloxy aldehyde substrates; Synthesis of 2-deoxy-2-C-phenylhexoses

Lookup NU author(s): Dr Michael HallORCiD

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Abstract

Silatropic carbonyl ene cyclisations of β-(allylsilyloxy)- and β-(crotylsilyloxy)butyraldehydes are shown to proceed with high stereoselectivity but at a much reduced rate in comparison to the cyclisation of analogous α-substrates. In the second section, olefin cross-metathesis is explored as a route to substituted α-(allylsilyloxy)aldehydes and the method applied to the synthesis of diastereomeric 2-deoxy- and 2-deoxy-2-C-phenyl hexose derivatives from butanediacetal-protected d-glyceraldehyde. © The Royal Society of Chemistry 2008.

Publication metadata

Author(s): Robertson J, Green SP, Hall MJ, Tyrrell AJ, Unsworth WP

Publication type: Article

Publication status: Published

Journal: Organic and Biomolecular Chemistry

Year: 2008

Volume: 6

Issue: 14

Pages: 2628-2635

Print publication date: 01/01/2008

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b804752a

DOI: 10.1039/b804752a

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