Stereospecific benzyne-induced olefination from β-amino alcohols and its application to the total synthesis of (-)-1-deoxy-D-fructose

Jih Ru Hwu; Yung Chang Hsu

doi:10.1002/chem.201001735

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Stereospecific benzyne-induced olefination from β-amino alcohols and its application to the total synthesis of (-)-1-deoxy-D-fructose

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Stereospecific benzyne-induced olefination from β-amino alcohols and its application to the total synthesis of (-)-1-deoxy-D-fructose

Jih Ru Hwu and Yung Chang Hsu

Chemistry - A European Journal, Vol.17(17), pp.4727-4731

18/04/2011

DOI: https://doi.org/10.1002/chem.201001735

Appears in keyword about Chemistry

Abstract

amino alcohols

benzyne

olefination

stereospecificity

total synthesis

'Ole in one! Treatment of β-amino alcohols with CS ₂ under alkaline conditions gave 1,3-thiazolidine-2-thiones, which were then treated with benzyne generated in situ. The reaction underwent an unprecedented addition-elimination process to give the desired olefins in 60-87 yields (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Title: Stereospecific benzyne-induced olefination from β-amino alcohols and its application to the total synthesis of (-)-1-deoxy-D-fructose
Creators - without role: Jih Ru Hwu - National Central University
Yung Chang Hsu - National Tsing Hua University
Identifiers: 9957770832806774
Academic Unit: National Tsing Hua University
Language: English
Resource Type: Journal article
Publication Details: Chemistry - A European Journal, Vol.17(17), pp.4727-4731

Stereospecific benzyne-induced olefination from β-amino alcohols and its application to the total synthesis of (-)-1-deoxy-D-fructose

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