Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones

Scott A. Steiger; Chun Li; Charles F. Campana; Nicholas R. Natale

doi:10.1016/j.tetlet.2015.12.038

Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones

Scott A. Steiger, Chun Li, Charles F. Campana, Nicholas R. Natale

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

15 Scopus citations

Abstract

The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity.

Original language	English
Pages (from-to)	423-425
Number of pages	3
Journal	Tetrahedron Letters
Volume	57
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2015.12.038
State	Published - Jan 20 2016

Funding

The authors are grateful to the Center for Structural and Functional Neuroscience for NIH NCRR P20RR015583 and NINDS R15 NS038444 for support of this work.

Funder number
P20RR015583
R15 NS038444

Keywords

Asymmetric organocatalysis
Dihydropyridine
Isoxazole
Lanthanide catalysis
Quinolone

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10.1016/j.tetlet.2015.12.038

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title = "Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones",

abstract = "The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity.",

keywords = "Asymmetric organocatalysis, Dihydropyridine, Isoxazole, Lanthanide catalysis, Quinolone",

author = "Steiger, \{Scott A.\} and Chun Li and Campana, \{Charles F.\} and Natale, \{Nicholas R.\}",

year = "2016",

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doi = "10.1016/j.tetlet.2015.12.038",

language = "English",

volume = "57",

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journal = "Tetrahedron Letters",

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T1 - Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones

AU - Steiger, Scott A.

AU - Li, Chun

AU - Campana, Charles F.

AU - Natale, Nicholas R.

PY - 2016/1/20

Y1 - 2016/1/20

N2 - The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity.

AB - The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity.

KW - Asymmetric organocatalysis

KW - Dihydropyridine

KW - Isoxazole

KW - Lanthanide catalysis

KW - Quinolone

UR - https://www.scopus.com/pages/publications/84953348693

U2 - 10.1016/j.tetlet.2015.12.038

DO - 10.1016/j.tetlet.2015.12.038

M3 - Article

AN - SCOPUS:84953348693

SN - 0040-4039

VL - 57

SP - 423

EP - 425

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones

Abstract

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Keywords

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