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Molecules 2005, 10(2), 383-393; doi:10.3390/10020383
Article

Diastereoselective Synthesis of 2-Phenylselenenyl-1,3-anti-Diols and 2-Phenylselenenyl-1,3-anti-Azido-Alcohols via Hydroxyand Azido-Selenenylation Reactions

, , * ,  and
Dipartimento di Chimica Organica “E. Paternò”, Università di Palermo, Viale delle Scienze, Parcod’Orleans II, Pad. 17, 90128, Palermo, Italy
* Author to whom correspondence should be addressed.
Received: 12 November 2004 / Revised: 18 November 2004 / Accepted: 19 November 2004 / Published: 28 February 2005
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Abstract

A method to synthesize 2-phenylselenenyl-1,3-anti-diols and 2-phenyl- selenenyl-1,3-anti-azidoalcohols via hydroxy- or azido-selenenylation of trans-allylic alcohols is reported. Moreover, the first example of hydroxyl-selenenylation of an allylic azide is presented. Yields ranging from moderate to good and diastereomeric ratios up to 95:5 are achieved.
Keywords: Azides; diols; seleniraniun ion. Azides; diols; seleniraniun ion.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Riela, S.; Aprile, C.; Gruttadauria, M.; Meo, P.L.; Noto, R. Diastereoselective Synthesis of 2-Phenylselenenyl-1,3-anti-Diols and 2-Phenylselenenyl-1,3-anti-Azido-Alcohols via Hydroxyand Azido-Selenenylation Reactions. Molecules 2005, 10, 383-393.

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