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Stereospecific Benzyne‐Induced Olefination from β‐Amino Alcohols and Its Application to the Total Synthesis of (−)‐1‐Deoxy‐ D ‐fructose
Author(s) -
Hwu Jih Ru,
Chang Hsu Yung
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001735
Subject(s) - aryne , chemistry , stereospecificity , organic chemistry , medicinal chemistry , stereochemistry , catalysis
'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).