Publications de Xiaogen Huang | EPFL Graph Search

Use of sultines in the asymmetric synthesis of polypropionate antibiotics

Pierre Vogel, Maris Turks, Cotinica Craita, Freddy Fonquerne, Laure Bouchez, Christopher Flowers, Xiaogen Huang

At low temperature and in the presence of an acid catalyst, SO2 adds to 1,3-dienes equilibrating with the corresponding 3,6-dihydro-1,2-oxathiin-2-oxides (sultines). These compounds are unstable above -60 degrees C and equilibrate with the more stable 2,5- ...

De Gruyter2008

Expeditious asymmetric synthesis of a stereoheptad corresponding to the C(19)-C(27)-ansa chain of rifamycins: Formal total synthesis of Rifamycin S

Pierre Vogel, Maris Turks, Xiaogen Huang

In the presence of sulfur dioxide and an acid promoter, (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenyleth- oxy)penta-1,3-dien-3-yl isobutyrate reacts with (Z)-3-(trimethylsilyloxy)-pent-2-ene giving a silyl sulfinate intermediate that undergoes, in the presence of ...

2005

Silyl methallylsulfinates: efficient and powerful agents for the chemoselective silylation of alcohols, polyols, phenols and carboxylic acids

Pierre Vogel, Loay Awad, Cotinica Craita, Xiaogen Huang

Alcohols, phenols and carboxylic acids are silylated with very good yields in the presence of silyl methallylsulfinates under non- basic conditions and with the formation of volatile co-products. ...

Royal Society of Chemistry2005

New developments on silyl 2-alkenyl sulfinates and their applications to the asymmetric synthesis of polypropionate fragments

Xiaogen Huang

Sulphur dioxide reacts with 1-oxydienes generating zwitterions which are quenched by enoxysilanes to form substituted silyl alkenylsulfinates. These intermediates are desilylated with Bu4NF and the resulting sulfinates react with MeI giving the correspondi ...

EPFL2004