Regiospecific control of additions of 4-substituted 3,5-dimethylisoxazoles to α,β unsaturated carbonyls

J. R. Stenzel; N. R. Natale

doi:10.1055/s-1997-1315

Regiospecific control of additions of 4-substituted 3,5-dimethylisoxazoles to α,β unsaturated carbonyls

J. R. Stenzel, N. R. Natale

University of Idaho

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4 Scopus citations

Abstract

Transmetalation of C-5-lithiomethylisoxazoles with the lower-order cuprate reagent lithium thienylcyanocuprate (Li[ThCuCN]) in THF results in exclusive conjugate addition to α,β-unsaturated carbonyls. In contrast, transmetalation with samarium tris(hexamethyldisilazide) (Sm[HMDS]₃) in diethyl ether directs 1,2-carbonyl addition. In both cases, optimum results were realized with a 4,5-dihydro-4,4-dimethyl-Δ²-2-oxazoline substituent at the C-4 position of the isoxazole.

Original language	English
Pages (from-to)	1041-1044
Number of pages	4
Journal	Synthesis
Issue number	9
DOIs	https://doi.org/10.1055/s-1997-1315
State	Published - 1997

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title = "Regiospecific control of additions of 4-substituted 3,5-dimethylisoxazoles to α,β unsaturated carbonyls",

abstract = "Transmetalation of C-5-lithiomethylisoxazoles with the lower-order cuprate reagent lithium thienylcyanocuprate (Li[ThCuCN]) in THF results in exclusive conjugate addition to α,β-unsaturated carbonyls. In contrast, transmetalation with samarium tris(hexamethyldisilazide) (Sm[HMDS]3) in diethyl ether directs 1,2-carbonyl addition. In both cases, optimum results were realized with a 4,5-dihydro-4,4-dimethyl-Δ2-2-oxazoline substituent at the C-4 position of the isoxazole.",

author = "Stenzel, \{J. R.\} and Natale, \{N. R.\}",

year = "1997",

doi = "10.1055/s-1997-1315",

language = "English",

pages = "1041--1044",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "9",

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T1 - Regiospecific control of additions of 4-substituted 3,5-dimethylisoxazoles to α,β unsaturated carbonyls

AU - Stenzel, J. R.

AU - Natale, N. R.

PY - 1997

Y1 - 1997

N2 - Transmetalation of C-5-lithiomethylisoxazoles with the lower-order cuprate reagent lithium thienylcyanocuprate (Li[ThCuCN]) in THF results in exclusive conjugate addition to α,β-unsaturated carbonyls. In contrast, transmetalation with samarium tris(hexamethyldisilazide) (Sm[HMDS]3) in diethyl ether directs 1,2-carbonyl addition. In both cases, optimum results were realized with a 4,5-dihydro-4,4-dimethyl-Δ2-2-oxazoline substituent at the C-4 position of the isoxazole.

AB - Transmetalation of C-5-lithiomethylisoxazoles with the lower-order cuprate reagent lithium thienylcyanocuprate (Li[ThCuCN]) in THF results in exclusive conjugate addition to α,β-unsaturated carbonyls. In contrast, transmetalation with samarium tris(hexamethyldisilazide) (Sm[HMDS]3) in diethyl ether directs 1,2-carbonyl addition. In both cases, optimum results were realized with a 4,5-dihydro-4,4-dimethyl-Δ2-2-oxazoline substituent at the C-4 position of the isoxazole.

UR - https://www.scopus.com/pages/publications/0030865696

U2 - 10.1055/s-1997-1315

DO - 10.1055/s-1997-1315

M3 - Article

AN - SCOPUS:0030865696

SN - 0039-7881

SP - 1041

EP - 1044

JO - Synthesis

JF - Synthesis

IS - 9

ER -

Regiospecific control of additions of 4-substituted 3,5-dimethylisoxazoles to α,β unsaturated carbonyls

Abstract

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