Enantioselective Synthesis of a Tetrasubstituted Oxocane via a Double Diastereoselective Hetero Diels-Alder Reaction

Mercedes Martín; María M. Afonso; Antonio Galindo; J. Antonio Palenzuela

doi:10.1055/s-2001-9717

Synlett 2001; 2001(1): 0117-0119
DOI: 10.1055/s-2001-9717

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Enantioselective Synthesis of a Tetrasubstituted Oxocane via a Double Diastereoselective Hetero Diels-Alder Reaction

Mercedes Martín^* , María M. Afonso, Antonio Galindo, J. Antonio Palenzuela

^*Instituto Universitario de Bio-Orgánica "Antonio González", Universidad de La Laguna, E-38206 La Laguna, Tenerife, Spain; Fax +349 22 63 00 95; E-mail: jpalenz@ull.es

Abstract

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A procedure for the enantioselective preparation of tetra-substituted medium sized cyclic ethers is presented. An oxocane is prepared by a sequence which involves a double diastereoselective hetero Diels-Alder reaction between a chiral aldehyde and a diene bearing an allylic chiral centre. The cycloadduct is transformed into a linear ether which is then converted to the cyclic ether by a highly regioselective intramolecular alkylation of a lithiosulfone with an epoxide. The sense of induction of the chiral centre on the diene is discussed.

hetero Diels-Alder reaction - double diastereoselectivity - intramolecular alkylation - cyclic ethers

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