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...

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Published inTetrahedron: asymmetry Vol. 11; no. 18; pp. 3769 - 3777
Main Authors Jordá-Gregori, Joan Miquel, González-Rosende, Maria Eugenia, Cava-Montesinos, Patricia, Sepúlveda-Arques, José, Galeazzi, Roberta, Orena, Mario
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.09.2000
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
ACID
SEMIEMPIRICAL METHODS
SERINE
AM1
IODOCYCLIZATION
OPTIMIZATION
OXAZOLIDIN-2-ONES
PARAMETERS
STEREOSELECTIVE SYNTHESIS
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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