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Issue 13, 2014
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Reactions of enantiopure cyclic diols with sulfuryl chloride

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Abstract

Monocyclic allylic cis-1,2-diols reacted with sulfuryl chloride at 0 °C in a regio- and stereo-selective manner to give 2-chloro-1-sulfochloridates, which were hydrolysed to yield the corresponding trans-1,2-chlorohydrins. At −78 °C, with very slow addition of sulfuryl chloride, cyclic sulfates were formed in good yields, proved to be very reactive with nucleophiles and rapidly decomposed on attempted storage. Reaction of a cyclic sulfate with sodium azide yielded a trans-azidohydrin without evidence of allylic rearrangement occurring. An enantiopure bicyclic cis-1,2-diol reacted with sulfuryl chloride to give, exclusively, a trans-1,2-dichloride enantiomer with retention of configuration at the benzylic centre and inversion at the non-benzylic centre; a mechanism is presented to rationalise the observation.

Graphical abstract: Reactions of enantiopure cyclic diols with sulfuryl chloride

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Supplementary files

Article information


Submitted
07 Jan 2014
Accepted
11 Feb 2014
First published
26 Feb 2014

Org. Biomol. Chem., 2014,12, 2128-2136
Article type
Paper
Author version available

Reactions of enantiopure cyclic diols with sulfuryl chloride

D. R. Boyd, N. D. Sharma, M. Kaik, P. B. A. M<small xmlns="http://www.rsc.org/schema/rscart38"> <sup>c</sup> </small>Intyre, J. F. Malone and P. J. Stevenson, Org. Biomol. Chem., 2014, 12, 2128
DOI: 10.1039/C4OB00042K

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