Asymmetric addition of aldehydes and ketones to chiral 2-azapentadienyl lithium compounds: Diastereoselective synthesis of 4-vinyl-4,5-dihydro-oxazoles

被引：0

作者：

Vossmann, P. ^{[1
]}

Hornig, K. ^{[1
]}

Fröhlich, R. ^{[1
]}

Würthwein, E.-U. ^{[1
]}

机构：

[1] Institut für Organische Chemie, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany

来源：

Synthesis | 2001年 / 09期

关键词：

Addition reactions - Aldehydes - Ketones - Nuclear magnetic resonance spectroscopy - Stereochemistry - X ray diffraction;

D O I：

10.1055/s-2001-15227

中图分类号：

学科分类号：

摘要：

Chiral 2-azapentadienyl lithium compounds 1, easily available by deprotonation of the corresponding N-allylimines 2, react with symmetrical and asymmetrical ketones and aldehydes to form new chiral, vinyl-substituted 4,5-dihydro-oxazoles 3. The structural properties of 1 in the gas phase and in solution were studied by quantum chemical calculations and NMR spectroscopy. The X-ray diffraction structure of 4,5-dihydro-oxazole 3d indicates the formation of a benzhydrol adduct. The new reactions are interpreted in terms of regioselective, stepwise additions of the carbonyl compounds to carbon atom C3 of 1 and subsequent removal of the chiral nucleofugal group.

引用

页码：1415 / 1426

共 21 条

[1] Asymmetric addition of aldehydes and ketones to chiral 2-azapentadielnyl lithium compounds:: Diastereoselective synthesis of 4-vinyl-4,5-dihydrooxazoles
Vossmann, P
Homig, K
Fröhlich, R
Würthwein, EU
SYNTHESIS-STUTTGART, 2001, (09): : 1415 - 1426
[2] Asymmetric addition of aldehydes and ketones to chiral 2-azapentadielnyl lithium compounds.: Diastereoselective synthesis of 4-vinyl-4, 5-dihydrooxazoles (July, 1415, 2001)
Vossmann, P
Horning, K
Fröhlich, R
Würthwein, EU
SYNTHESIS-STUTTGART, 2002, (11): : 1624 - 1624
[3] Asymmetric alkylation of chiral 2-azapentadienyl metal compounds: Diastereoselective synthesis of alkyl-substituted N-allylimines (2-aza-1,4-pentadienes)
Stakemeier, H
Wurthwein, EU
LIEBIGS ANNALEN, 1996, (11): : 1833 - 1843
[4] Asymmetric Synthesis of 2,3-Dihydro-4-pyranones by Reaction of Chiral 3-Alkoxycyclobutanone and Aldehydes
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ORGANIC LETTERS, 2010, 12 (21) : 4984 - 4987
[5] Asymmetric addition of chiral 1,3,2-benzoxazaphosphinine 2-oxides to aldehydes:: Diastereoselective synthesis of α-substituted β-hydroxyphosphonic acids
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Maestro, Alicia
Pedrosa, Rafael
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (18) : 3012 - 3022
[6] Asymmetric synthesis of 3,4-annulated cyclopentenones from cycloalkenyl ketones and vinyl carbamates by diastereoselective carbonyl addition/conrotatory 4π ring closure
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Froehlich, Roland
Hoppe, Dieter
SYNTHESIS-STUTTGART, 2008, (14): : 2264 - 2270
[7] Asymmetric synthesis of multi-substituted indolizidines by intramolecular addition of allylsilane to chiral 2,3-dihydro-4-pyridones
Furman, B
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POLISH JOURNAL OF CHEMISTRY, 2005, 79 (12) : 1919 - 1928
[8] Diastereoselective addition of chiral (2-lithiophenyl)acetaldehyde acetals to various imines as key step in the asymmetric synthesis of 1-aryltetrahydroisoquinolines, Part 4
Wünsch, B
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (02) : 503 - 517
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Taketoshi, Ayako
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CHEMISTRY LETTERS, 2007, 36 (01) : 64 - 65
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LURZ, CJ
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