A domino reaction, based on an organocatalyzed sulfa-Michael-Michael sequence, demonstrated to be useful for the asymmetric synthesis of spiro[pyrazolone-4,3’-tetrahydrothiophenes], bearing three consecutive stereocenters. This new class of spirocyclic compounds has been synthesized in good yield, fairly good diastereo- and enantioselectivity by reacting alpha-unsaturated pyrazolones and trans-tert-butyl 4-mercapto-2-butenoate in the presence of a readily available secondary amine thiourea derived from (R,R)-1,2-diphenyl ethylenediamine.
Amine thiourea catalysed double Michael reaction: an approach for the asymmetric synthesis of spiro[pyrazolone-4,3'-tetrahydrothiophenes]
MENINNO, SARA;LATTANZI, Alessandra;
2017-01-01
Abstract
A domino reaction, based on an organocatalyzed sulfa-Michael-Michael sequence, demonstrated to be useful for the asymmetric synthesis of spiro[pyrazolone-4,3’-tetrahydrothiophenes], bearing three consecutive stereocenters. This new class of spirocyclic compounds has been synthesized in good yield, fairly good diastereo- and enantioselectivity by reacting alpha-unsaturated pyrazolones and trans-tert-butyl 4-mercapto-2-butenoate in the presence of a readily available secondary amine thiourea derived from (R,R)-1,2-diphenyl ethylenediamine.File in questo prodotto:
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