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

14 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

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.}",

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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

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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

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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

Keywords

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