Tetrahedron

New synthetic applications of organotin compounds: synthesis of stereodefined 2-iodo-2-alkenones, 2-substituted (E)-2-alkenones and 2-methyl-2-cycloalkenones

F Bellina, A Carpita, D Ciucci, M De Santis, R Rossi

Index: Bellina, Fabio; Carpita, Adriano; Ciucci, Donatella; De Santis, Massimo; Rossi, Renzo Tetrahedron, 1993 , vol. 49, # 21 p. 4677 - 4698

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Citation Number: 42

Abstract

Stereoisomeric mixtures of 3-iodo-3-nonen-2-one, 8a, 2-iodo-1-phenyl-2-octen-1-one, 8b, 2- iodo-1, 3-diphenyl-2-propen-1-one, 8c, as well as (Z)-3-iodo-4-phenyl-3-buten-2-one, 8d, have been efficiently synthesized by a reaction sequence involving a Pd-catalyzed reaction between the corresponding 1-alkynyl ketones, 10, and Bu3SnH followed by iododestannylation. Stereomutation experiments carried out in the presence of daylight ...