The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde

Jared K. Nelson; Brendan Twamley; Trinidad J. Villalobos; Nicholas R. Natale

doi:10.1016/j.tetlet.2008.07.169

The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde

Jared K. Nelson, Brendan Twamley, Trinidad J. Villalobos, Nicholas R. Natale

University of Idaho

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

8 Scopus citations

Abstract

Nucleophilic addition of alkyl- and aryl-zinc reagents to a C(4) functionalized isoxazolyl aldehyde proceeded effectively with high enantioselectivity (85-94% ee). The amino alcohol catalyst (S)-2-piperidinyl-1,1,2-triphenyl ethanol (10) afforded the (R)-product 2b, as established by X-ray crystallography.

Original language	English
Pages (from-to)	5957-5960
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2008.07.169
State	Published - Oct 6 2008

Funding

The authors thank NIH for grants NS038444(NN), P20RR015583(NN), P20RR16454(JKN), the Fraternal Order of Eagles Alzheimer’s Fund (NN), and the Malcolm and Carol Renfrew Scholarship (JKN). 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. We thank Rakesh Kumar and Shikha Sharma for technical assistance.

Funder number
P20RR16454, P20RR015583, NS038444

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10.1016/j.tetlet.2008.07.169

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title = "The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde",

abstract = "Nucleophilic addition of alkyl- and aryl-zinc reagents to a C(4) functionalized isoxazolyl aldehyde proceeded effectively with high enantioselectivity (85-94\% ee). The amino alcohol catalyst (S)-2-piperidinyl-1,1,2-triphenyl ethanol (10) afforded the (R)-product 2b, as established by X-ray crystallography.",

author = "Nelson, \{Jared K.\} and Brendan Twamley and Villalobos, \{Trinidad J.\} and Natale, \{Nicholas R.\}",

note = "Funding Information: The authors thank NIH for grants NS038444(NN), P20RR015583(NN), P20RR16454(JKN), the Fraternal Order of Eagles Alzheimer{\textquoteright}s Fund (NN), and the Malcolm and Carol Renfrew Scholarship (JKN). 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. We thank Rakesh Kumar and Shikha Sharma for technical assistance. ",

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doi = "10.1016/j.tetlet.2008.07.169",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde

AU - Nelson, Jared K.

AU - Twamley, Brendan

AU - Villalobos, Trinidad J.

AU - Natale, Nicholas R.

N1 - Funding Information: The authors thank NIH for grants NS038444(NN), P20RR015583(NN), P20RR16454(JKN), the Fraternal Order of Eagles Alzheimer’s Fund (NN), and the Malcolm and Carol Renfrew Scholarship (JKN). 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. We thank Rakesh Kumar and Shikha Sharma for technical assistance.

PY - 2008/10/6

Y1 - 2008/10/6

N2 - Nucleophilic addition of alkyl- and aryl-zinc reagents to a C(4) functionalized isoxazolyl aldehyde proceeded effectively with high enantioselectivity (85-94% ee). The amino alcohol catalyst (S)-2-piperidinyl-1,1,2-triphenyl ethanol (10) afforded the (R)-product 2b, as established by X-ray crystallography.

AB - Nucleophilic addition of alkyl- and aryl-zinc reagents to a C(4) functionalized isoxazolyl aldehyde proceeded effectively with high enantioselectivity (85-94% ee). The amino alcohol catalyst (S)-2-piperidinyl-1,1,2-triphenyl ethanol (10) afforded the (R)-product 2b, as established by X-ray crystallography.

UR - https://www.scopus.com/pages/publications/50049119913

U2 - 10.1016/j.tetlet.2008.07.169

DO - 10.1016/j.tetlet.2008.07.169

M3 - Article

AN - SCOPUS:50049119913

SN - 0040-4039

VL - 49

SP - 5957

EP - 5960

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde

Abstract

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