C(1)-substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

Raymond L. Funk; Ge Yang

doi:10.1016/S0040-4039(98)02627-6

C(1)-substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

Raymond L. Funk, Ge Yang

Chemistry

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13 Scopus citations

Abstract

C(1)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the β-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee.

Original language	English (US)
Pages (from-to)	1073-1074
Number of pages	2
Journal	Tetrahedron Letters
Volume	40
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(98)02627-6
State	Published - Feb 5 1999

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)02627-6

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title = "C(1)-substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones",

abstract = "C(1)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the β-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee.",

author = "Funk, {Raymond L.} and Ge Yang",

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T1 - C(1)-substituted menthol derivatives

T2 - Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

AU - Funk, Raymond L.

AU - Yang, Ge

PY - 1999/2/5

Y1 - 1999/2/5

N2 - C(1)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the β-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee.

AB - C(1)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the β-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee.

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U2 - 10.1016/S0040-4039(98)02627-6

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

C(1)-substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

Abstract

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