On the [3 + 2] annulation of cyclic allylsilanes with N-phenyltriazolinedione: an enantio- and diastereoselective synthesis of cis-1,3-diaminocyclitols

Raudra T Dey; Tarun K Sarkar

doi:10.1021/jo100724w

On the [3 + 2] annulation of cyclic allylsilanes with N-phenyltriazolinedione: an enantio- and diastereoselective synthesis of cis-1,3-diaminocyclitols

J Org Chem. 2010 Jul 2;75(13):4521-9. doi: 10.1021/jo100724w.

Authors

Raudra T Dey¹, Tarun K Sarkar

Affiliation

¹ Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India.

PMID: 20518576
DOI: 10.1021/jo100724w

Abstract

Improved conditions were found to trigger [3 + 2] annulation of cyclic allylsilanes with N-phenyltriazolinedione (PTAD); the products from this reaction were readily tailored into cis-1,3-diaminocyclitols in highly enantioenriched form with full stereochemical control of up to four contiguous stereogenic centers.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Cyclitols / chemical synthesis*
Cyclitols / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Silanes / chemistry*
Stereoisomerism
Triazoles / chemistry*

Substances

Alkenes
Cyclitols
Silanes
Triazoles
allylsilane