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Formation of δ-Sultines (1,2-Oxathiane 2-Oxides) from Thiolane 1-Oxides (1999)

Schuler, Barbara ; Voss, Jürgen

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 943-947

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ISSN: 1434-193X

Keywords: Thiolane 1-oxides ; Oxidations ; δ-Sultines ; [Bis(trifluoroacetoxy)iodo]benzene ; Asymmetric synthesis ; Carbanions ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: -2-(Alkylthio)-2-benzylthiolane 1-oxides (1a, b) and 2-(alkylthio)-2-(α-hydroxybenzyl)thiolane 1-oxides (1c, d) are oxidized with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Under ring enlargement the corresponding cyclic sulfinate esters (δ-sultines) 2 are formed. Only (1R*,2S*)-1b is reactive whereas (1R*,2R*)-1b is not attacked. This observation is explained with the formation of a cyclic intermediate 3.

Type of Medium: Electronic Resource

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