New Approach to Sugar Dienes; Useful Building Blocks for the Synthesis of 
Bicyclic Derivatives

Grzegorz Witkowski; Sławomir Jarosz

doi:10.1055/s-0033-1339374

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(14): 1813-1817
DOI: 10.1055/s-0033-1339374

letter

New Approach to Sugar Dienes; Useful Building Blocks for the Synthesis of Bicyclic Derivatives

Grzegorz Witkowski

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland Fax: +48(22)6326681 eMail: slawomir.jarosz@icho.edu.pl

,

Sławomir Jarosz*

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland Fax: +48(22)6326681 eMail: slawomir.jarosz@icho.edu.pl

› Institutsangaben

Abstract

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Abstract

A sugar aldehyde with silyl protection at C1, readily prepared from methyl α-d-glucopyranoside, reacted with allylborate or allylchromium reagents to afford the corresponding (anti) adducts, which were selectively converted into either E- or Z-diene. Deprotection of the anomeric position with TBAF proceeded in excellent yield, and further functionalization of the resulting hemiacetal led to the formation of complex bicyclic products such as highly functionalized oxazolidines.

Key words

carbohydrates - chiral pool - cycloaddition - stereoselective synthesis - protecting groups

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Referenzen

References and Notes

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