Tetrahedron p. 10525 - 10546 (1996)
Update date:2022-08-03
Topics:
Villar, Juan Manuel
Delgado, Antonio
Llebaria, Amadeu
Moreto, Josep M.
Molins, Elies
Miravitlles, Carles
Different approaches to the asymmetric synthesis of cyclopentenones by means of the Ni(CO)4-promoted alkyne-allyl halide cyclization-carbonylation are reported. The use of acetylenic sulfoxides 1 has proved effective for the synthesis of acyclic, fused [5+8], and spiro [5+5], [5+7], and [5+8] cyclopentenones, whereas placement of the aryl sulfoxide on the allylic system failed to afford any cycloadduct. Homochiral fused [5+8], and spiro [5+7] and [5+8] cyclopentenones have been obtained by this methodology. Finally, a modest enantioselectivity was observed when different homochiral α-substituted carboxylates were used as ligands in our reaction system.
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(1996)Doi:10.1016/0040-4020(96)00657-6
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(2019)