Syntheses of highly constrained β-aryl isohexanoic acid derivatives via asymmetric Michael addition

Subo Liao; Yinglin Han; Wei Qiu; Michael Bruck; Victor J. Hruby

doi:10.1016/0040-4039(96)01795-9

Syntheses of highly constrained β-aryl isohexanoic acid derivatives via asymmetric Michael addition

Subo Liao, Yinglin Han, Wei Qiu, Michael Bruck, Victor J. Hruby

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

A series of enantiomerically pure highly sterically hindered β-branched isohexanoic acid derivatives have been synthesized with high diastereoselectivity via asymmetric Michael addition. The X-ray crystal structure of (4S,3'S)-3-[3'-(2,6-dimethylphenyl)isohexanyl]-4-phenyl-2-oxazolidinon e demonstrated that the β-configuration was induced from the Si-face, and that the torsional angle χ₂ was restricted by the bulky β-isopropyl group to the range expected from molecular modeling.

Original language	English (US)
Pages (from-to)	7917-7920
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	44
DOIs	https://doi.org/10.1016/0040-4039(96)01795-9
State	Published - Oct 28 1996
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "A series of enantiomerically pure highly sterically hindered β-branched isohexanoic acid derivatives have been synthesized with high diastereoselectivity via asymmetric Michael addition. The X-ray crystal structure of (4S,3'S)-3-[3'-(2,6-dimethylphenyl)isohexanyl]-4-phenyl-2-oxazolidinon e demonstrated that the β-configuration was induced from the Si-face, and that the torsional angle χ2 was restricted by the bulky β-isopropyl group to the range expected from molecular modeling.",

author = "Subo Liao and Yinglin Han and Wei Qiu and Michael Bruck and Hruby, {Victor J.}",

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T1 - Syntheses of highly constrained β-aryl isohexanoic acid derivatives via asymmetric Michael addition

AU - Liao, Subo

AU - Han, Yinglin

AU - Qiu, Wei

AU - Bruck, Michael

AU - Hruby, Victor J.

N1 - Funding Information: about this research, and the financial support of grants from NIDA

PY - 1996/10/28

Y1 - 1996/10/28

N2 - A series of enantiomerically pure highly sterically hindered β-branched isohexanoic acid derivatives have been synthesized with high diastereoselectivity via asymmetric Michael addition. The X-ray crystal structure of (4S,3'S)-3-[3'-(2,6-dimethylphenyl)isohexanyl]-4-phenyl-2-oxazolidinon e demonstrated that the β-configuration was induced from the Si-face, and that the torsional angle χ2 was restricted by the bulky β-isopropyl group to the range expected from molecular modeling.

AB - A series of enantiomerically pure highly sterically hindered β-branched isohexanoic acid derivatives have been synthesized with high diastereoselectivity via asymmetric Michael addition. The X-ray crystal structure of (4S,3'S)-3-[3'-(2,6-dimethylphenyl)isohexanyl]-4-phenyl-2-oxazolidinon e demonstrated that the β-configuration was induced from the Si-face, and that the torsional angle χ2 was restricted by the bulky β-isopropyl group to the range expected from molecular modeling.

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M3 - Article

AN - SCOPUS:0030605167

SN - 0040-4039

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EP - 7920

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Syntheses of highly constrained β-aryl isohexanoic acid derivatives via asymmetric Michael addition

Abstract

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