Synthetic utility of epoxides for chiral functionalization of isoxazoles

Jared K. Nelson; Christopher T. Burns; Miles P. Smith; Brendan Twamley; N. R. Natale

doi:10.1016/j.tetlet.2008.03.059

Synthetic utility of epoxides for chiral functionalization of isoxazoles

Jared K. Nelson, Christopher T. Burns, Miles P. Smith, Brendan Twamley, N. R. Natale

University of Idaho

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

3 Scopus citations

Abstract

The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100% inversion at the benzylic carbon to afford the (S)-alcohol (4b).

Original language	English
Pages (from-to)	3078-3082
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2008.03.059
State	Published - May 5 2008

Funding

The authors thank the National Institute of Neurological Disease and Stroke for the continuing support of Grant NS38444, and P20 RR015583. J.K.N. acknowledges INBRE Grant P20 RR16454 and the Malcolm and Carol Renfrew Scholarship Endowment, University of Idaho. The Bruker (Siemens) smart apex diffraction facility was established at the University of Idaho with the assistance of the nsf-epscor program and the M. J. Murdock Charitable Trust, Vancouver, WA, USA.

Funder number
NS38444, P20 RR015583, P20 RR16454

Access to Document

10.1016/j.tetlet.2008.03.059

Cite this

@article{29d66b869eb444369ce85f05f54614b8,

title = "Synthetic utility of epoxides for chiral functionalization of isoxazoles",

abstract = "The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100\% inversion at the benzylic carbon to afford the (S)-alcohol (4b).",

author = "Nelson, \{Jared K.\} and Burns, \{Christopher T.\} and Smith, \{Miles P.\} and Brendan Twamley and Natale, \{N. R.\}",

note = "Funding Information: The authors thank the National Institute of Neurological Disease and Stroke for the continuing support of Grant NS38444, and P20 RR015583. J.K.N. acknowledges INBRE Grant P20 RR16454 and the Malcolm and Carol Renfrew Scholarship Endowment, University of Idaho. The Bruker (Siemens) smart apex diffraction facility was established at the University of Idaho with the assistance of the nsf-epscor program and the M. J. Murdock Charitable Trust, Vancouver, WA, USA. ",

year = "2008",

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doi = "10.1016/j.tetlet.2008.03.059",

language = "English",

volume = "49",

pages = "3078--3082",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthetic utility of epoxides for chiral functionalization of isoxazoles

AU - Nelson, Jared K.

AU - Burns, Christopher T.

AU - Smith, Miles P.

AU - Twamley, Brendan

AU - Natale, N. R.

N1 - Funding Information: The authors thank the National Institute of Neurological Disease and Stroke for the continuing support of Grant NS38444, and P20 RR015583. J.K.N. acknowledges INBRE Grant P20 RR16454 and the Malcolm and Carol Renfrew Scholarship Endowment, University of Idaho. The Bruker (Siemens) smart apex diffraction facility was established at the University of Idaho with the assistance of the nsf-epscor program and the M. J. Murdock Charitable Trust, Vancouver, WA, USA.

PY - 2008/5/5

Y1 - 2008/5/5

N2 - The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100% inversion at the benzylic carbon to afford the (S)-alcohol (4b).

AB - The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100% inversion at the benzylic carbon to afford the (S)-alcohol (4b).

UR - https://www.scopus.com/pages/publications/41649100264

U2 - 10.1016/j.tetlet.2008.03.059

DO - 10.1016/j.tetlet.2008.03.059

M3 - Article

AN - SCOPUS:41649100264

SN - 0040-4039

VL - 49

SP - 3078

EP - 3082

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Synthetic utility of epoxides for chiral functionalization of isoxazoles

Abstract

Funding

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