One-Pot Synthesis of α-Substituted Hydroxylamine Derivatives from Aldehydes Using Lithium Perchlorate/Diethyl Ether as a Catalyst

Akbar Heydari; Morteza Mehrdad; Hossein Tavakol

doi:10.1055/s-2003-41454

SHORTPAPER

One-Pot Synthesis of α-Substituted Hydroxylamine Derivatives from Aldehydes Using Lithium Perchlorate/Diethyl Ether as a Catalyst

Akbar Heydari*^a, Morteza Mehrdad^b, Hossein Tavakol^a
^a Chemistry Department, Tarbiat Modarres University, P. O. Box 14155-4838, Tehran, Iran
Fax: +98(21)8006544; e-Mail: akbar.heydari@gmx.de;
^b Department of Phytochemistry, Shahid Beheshti University, Evin 1983963113, Tehran, Iran

Abstract

All articles of this category

Abstract

O-(Trimethylsilyl)oxime ethers, generated in situ by reaction of aldehydes and O-(trimethylsilyl)hydroxylamine in lithium perchlorate/diethyl ether solution, are highly reactive species and undergo facile reaction with silylated nucleophiles, such as trimethylsilyl cyanide and the binary reagent (MeO)₃P/Me₃SiCl, to give α-substituted hydroxylamine derivatives.

Key words

lithium perchlorate - oximes - α-substituted hydroxylamines

Full Text

References

<A NAME="RZ05903SS-1A">1a</A> Bloch R. Chem. Rev. 1998, 98: 1407

<A NAME="RZ05903SS-1B">1b</A> Enders D. Reinhold U. Tetrahedron: Asymmetry 1997, 8: 1895

<A NAME="RZ05903SS-2">2</A> Risch N. Arend N. In Stereoselective Synthesis (Houben-Weyl) Vol. 3: Helmchen G. Hoffmann RW. Mulzer J. Schaumann E. Thieme; Stuttgart: 1996. p.1833-2009

<A NAME="RZ05903SS-3A">3a</A> Moody CJ. Lightfoot AP. Gallagher PT. Synlett 1997, 659

<A NAME="RZ05903SS-3B">3b</A> Marco JA. Carda M. Murga J. Gonzalez F. Falomir E. Tetrahedron Lett. 1997, 38: 1841

<A NAME="RZ05903SS-3C">3c</A> Hanessian S. Yang R.-Y. Tetrahedron Lett. 1996, 37: 5237

<A NAME="RZ05903SS-3D">3d</A> Dieter RK. Datar R. Can. J. Chem. 1993, 71: 814

<A NAME="RZ05903SS-3E">3e</A> Kolasa T. Sharma SK. Miller MJ. Tetrahedron 1998, 44: 5431

<A NAME="RZ05903SS-3F">3f</A> Yamamoto Y. Ito W. Tetrahedron 1998, 44: 5415

<A NAME="RZ05903SS-3G">3g</A> Rodriques KE. Basha A. Summers JB. Brooks DW. Tetrahedron Lett. 1988, 29: 3455

<A NAME="RZ05903SS-3H">3h</A> Corey EJ. Nimura K. Konischi Y. Hashimoto S. Hamada Y. Tetrahedron Lett. 1986, 27: 2199

<A NAME="RZ05903SS-3I">3i</A> Pirie DK. Welch WM. Weeks PD. Volkmann RA. Tetrahedron Lett. 1986, 27: 1549

<A NAME="RZ05903SS-3J">3j</A> Ikeda K. Achiwa K. Sekiya M. Tetrahedron Lett. 1983, 24: 4707

<A NAME="RZ05903SS-3K">3k</A> Fiaud J.-C. Kagan HB. Tetrahedron Lett. 1971, 1019

<A NAME="RZ05903SS-4">4</A> Volkmann RA. In Comprehensive Organic Synthesis Vol. 1: Trost BM. Fleming I. Schreiber SL. Pergamon; Oxford: 1991. p.355-396

<A NAME="RZ05903SS-5">5</A> Itsuno S. Miyazaki K. Ito K. Tetrahedron Lett. 1986, 27: 3033

<A NAME="RZ05903SS-6">6</A> LiClO₄ in Et₂O has gained importance as a versatile reaction medium for effecting various organic transformations. For a review, see: Heydari A. Tetrahedron 2002, 58: 6777

<A NAME="RZ05903SS-7A">7a</A> Hashimoto M. inventors; US Patent, 4105156. ; Chem Abstr. 1980, 93, 150378

<A NAME="RZ05903SS-7B">7b</A> Kuroda Y, Okuhara M, Iguchi E, Aoki H, Imanaka H, Kamiya T, Hashimoto H, Hemmi K, and Takeno H. inventors; Ger.Offen. 2733658. ; Chem. Abstr. 1978, 89, 6413

<A NAME="RZ05903SS-7C">7c</A> Kamiya T. Hemmi K. Takeno H. Hashimoto M. Tetrahedron Lett. 1980, 21: 95

<A NAME="RZ05903SS-7D">7d</A> Hemmi K. Takeno H. Hashimoto M. Kamiya T. Chem. Pharm. Bull. 1982, 30: 111

<A NAME="RZ05903SS-8">8</A> Petrov KA. Treshchalina LV. Chizov VM. Zh. Obshch. Khim. 1979, 49: 590 ; Chem. Abstr. 1979, 91, 5305

<A NAME="RZ05903SS-9">9</A> Osipova MP. Lukin PM. Kukhtin VA. Zh. Obshch. Khim. 1982, 52: 449 ; Chem. Abstr. 1982, 96, 162861

<A NAME="RZ05903SS-10">10</A> Huber R. Knierzinger A. Obrecht JP. Vasella A. Helv. Chim. Acta 1985, 68: 1730

<A NAME="RZ05903SS-11">11</A> Elhaddadi M. Petrus JRC. Petrus F. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 57: 119

<A NAME="RZ05903SS-12">12</A> Yuan C. Chen S. Zhou H. Maier L. Synthesis 1993, 955

When a solution of aldehyde and O-(trimethylsilyl)hydroxyl-amine was treated with trimethyl phosphite/trimethylsilyl chloride in Et₂O in the absence of LPDE at r.t. for 4 h, the corresponding O-(trimethylsilyl)oxime ether product was obtained in high yield.

<A NAME="RZ05903SS-14A">14a</A> Evans DA. Hurst KM. Takacs JM. J. Am. Chem. Soc. 1978, 100: 3467

<A NAME="RZ05903SS-14B">14b</A> Okamoto Y. Azuhata T. Sakurai H. Chem. Lett. 1981, 1265

<A NAME="RZ05903SS-14C">14c</A> Okamoto Y. Sakurai H. Synthesis 1982, 497