2-Chloro-2-cyclopropylideneacetate 1 and spiropentane analog 2 cycloadd pyrroline N-oxide 3 to give spiro[cyclopropane- 1,5A-isoxazolidine]s 4 and 5 in good yields; due to the presence of a chlorine substituent on the carbon a to the spirocyclopropane ring, which facilitates a cyclopropyl to cyclobutyl ring enlargement, these compounds undergo a cascade rearrangement to yield indolizinone derivatives 8 and 9 cleanly (70–73% yield), offering a new method for the synthesis of the indolizine skeleton.

A New Cascade Ring Enlargement of Isoxazolidines Formed from 2-Chloro-2-cyclopropylideneacetates / C. Zorn; A. Goti; A. Brandi; K. Johnsen; S. I. Kozhushkov; A. de Meijere. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - STAMPA. - 1998:(1998), pp. 903-904.

A New Cascade Ring Enlargement of Isoxazolidines Formed from 2-Chloro-2-cyclopropylideneacetates

GOTI, ANDREA;BRANDI, ALBERTO;
1998

Abstract

2-Chloro-2-cyclopropylideneacetate 1 and spiropentane analog 2 cycloadd pyrroline N-oxide 3 to give spiro[cyclopropane- 1,5A-isoxazolidine]s 4 and 5 in good yields; due to the presence of a chlorine substituent on the carbon a to the spirocyclopropane ring, which facilitates a cyclopropyl to cyclobutyl ring enlargement, these compounds undergo a cascade rearrangement to yield indolizinone derivatives 8 and 9 cleanly (70–73% yield), offering a new method for the synthesis of the indolizine skeleton.
1998
1998
903
904
C. Zorn; A. Goti; A. Brandi; K. Johnsen; S. I. Kozhushkov; A. de Meijere
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/250588
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