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

doi:10.3390/10020383

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

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

Serena Riela, Carmela Aprile, Michelangelo Gruttadauria* , Paolo Lo Meo and Renato Noto

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; in revised form: 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.

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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.

AMA Style

Riela S, Aprile C, Gruttadauria M, Meo PL, 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(2):383-393.

Chicago/Turabian Style

Riela, Serena; Aprile, Carmela; Gruttadauria, Michelangelo; Meo, Paolo L.; Noto, Renato. 2005. "Diastereoselective Synthesis of 2-Phenylselenenyl-1,3-anti-Diols and 2-Phenylselenenyl-1,3-anti-Azido-Alcohols via Hydroxyand Azido-Selenenylation Reactions." Molecules 10, no. 2: 383-393.

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