1,3-Oxazin-2-ones vs tetrahydrofurans by iodocyclisation of 2-alkoxycarbonylamino-3-alken-1-ols

Iodocyclisation of primary homoallylic alcohols 2a– d, containing either a 2- t-butoxy- or a benzyloxycarbonylamino group, was studied, in order to establish the nucleophilic group involved in cyclofunctionalisation. In fact, the N- t-Boc derivative 2a gave the oxazinone 3, exclusively, whereas star...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 2000-09, Vol.11 (18), p.3769-3777
Main Authors: Jordá-Gregori, Joan Miquel, González-Rosende, Maria Eugenia, Cava-Montesinos, Patricia, Sepúlveda-Arques, José, Galeazzi, Roberta, Orena, Mario
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Iodocyclisation of primary homoallylic alcohols 2a– d, containing either a 2- t-butoxy- or a benzyloxycarbonylamino group, was studied, in order to establish the nucleophilic group involved in cyclofunctionalisation. In fact, the N- t-Boc derivative 2a gave the oxazinone 3, exclusively, whereas starting from the N-Cbz derivative 2b a diastereomeric mixture of substituted tetrahydrofurans 4 and 5 resulted in ratios depending upon the reaction conditions. These results were rationalised by means of computational methods. On the contrary, migration of both the t-butyl or benzyl group to the hydroxy group was observed when both 2c and 2d underwent cyclisation to give the corresponding 5-alkoxymethyl oxazolidin-2-ones 7a, b in low yield, but with high regio- and stereocontrol.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)00323-2