Enantioselective Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted (E)-2-oxobut-3-enoates

Gert Preegel; Kaja Ilmarinen; Ivar Järving; Tõnis Kanger; Tõnis Pehk; Margus Lopp

doi:10.1055/s-0035-1560347

Synthesis, Table of Contents

Synthesis 2015; 47(23): 3805-3812
DOI: 10.1055/s-0035-1560347

paper

Enantioselective Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted (E)-2-oxobut-3-enoates

Gert Preegel

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia

,

Kaja Ilmarinen

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia

,

Ivar Järving

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia

,

Tõnis Kanger

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia

,

Tõnis Pehk

^bNational Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia Email: margus.lopp@ttu.ee

,

Margus Lopp*

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia

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Abstract

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Abstract

An organocatalytic cascade Michael addition-cyclization reaction of cyclopentane-1,2-dione with substituted (E)-2-oxobut-3-enoates, creating two stereocenters and giving bicyclic hemiacetals 3 in excellent yield (up to 93%) and enantioselectivity (up to 96% ee) was developed. From 2-chlorophenyl-substituted (E)-2-oxobut-3-enoate, the adduct revealed pseudo-atropisomerism from the hindered rotation of the phenyl ring. The hemiacetal 3 was reduced with Et₃SiH and Lewis acid affording substituted 1,2-cyclopentanedione 8, and disilylated with an excess of TMSOTf and Et₃N to the dienol disilyl ether 9.

Key words

organocatalysis - cascade reactions - atropisomerism - stereoselectivity

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References

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