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Synthesis of chiral 2-oxo- and 2-thio-1,3,2-oxazaphospholidines via the asymmetric cyclization of l-serinoates with (thio)phosphoryl dichlorides

✍ Scribed by Zheng-Jie He; Wen-Bin Chen; Zheng-Hong Zhou; Chu-Chi Tang

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
147 KB
Volume
11
Category
Article
ISSN
1042-7163

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✦ Synopsis

In this article, we have described the asymmetric cyclization of L-serinoates and N-benzyl Lserinoate with phosphoro(no-)dichloridates or their thio-analog, respectively, and we have investigated the asymmetric induction effect of the chiral carbon center on the forming of a chiral phosphorus center. The diastereomeric excess percentages (de%) of the desired products 2-oxo-and 2-thio-1,3,2-oxazaphospholidines, are obtained based on their 31 P NMR data. In some cases, the cyclization products have been separated as pure diastereomers by column chromatography. Their configuration is preliminarily discussed.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Synthesis of Chiral
ChemInform Abstract: Synthesis of Chiral 2-Oxo- and 2-Thio-1,3,2-oxazaphospholidines via the Asymmetric Cyclization of L-Serinoates with (Thio)phosphoryl Dichlorides.
✍ Zheng-Jie He; Wen-Bin Chen; Zheng-Hong Zhou; Chu-Chi Tang πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 29 KB πŸ‘ 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a β€œFull Text” option. The original article is trackable v

ChemInform Abstract: Synthesis of Chiral
ChemInform Abstract: Synthesis of Chiral 2-Oxo- and 2-Thio-1,3,2-oxazaphospholidines via the Asymmetric Cyclization of L-Serinoates with (Thio)phosphoryl Dichlorides.
✍ Zheng-Jie He; Wen-Bin Chen; Zheng-Hong Zhou; Chu-Chi Tang πŸ“‚ Article πŸ“… 2000 πŸ› John Wiley and Sons βš– 30 KB πŸ‘ 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a β€œFull Text” option. The original article is trackable v

Synthesis of novel chiral 2-oxo- and 2-t
Synthesis of novel chiral 2-oxo- and 2-thio-1,3,2-oxazaphospholidines via asymmetric cyclization of L-methionol with (thio)phosphoryl dichlorides
✍ Ling-yan Liu; Ru-yu Chen; You Huang πŸ“‚ Article πŸ“… 2005 πŸ› John Wiley and Sons 🌐 English βš– 102 KB πŸ‘ 1 views

## Abstract In order to search for novel antitumor and antiviral agents with high activity and low toxicity, a series of chiral 2‐thio(oxo)‐1,3,2‐oxazaphospholidines were synthesized via the reaction of L‐methionol with all kinds of (thio)phosphoryl dichlorides in THF in the presence of triethylami