l-Proline-Catalyzed One-Pot Three-Component Reaction for the Synthesis of β-Alkoxy Ketones

Rajasekhar Dodda; Cong-Gui Zhao

doi:10.1055/s-2006-950184

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l-Proline-Catalyzed One-Pot Three-Component Reaction for the Synthesis of β-Alkoxy Ketones

Rajasekhar Dodda, Cong-Gui Zhao*
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, Texas 78249-0698, USA
Fax: +1(210)5587428; e-Mail: cong.zhao@utsa.edu;

Abstract

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Abstract

β-Alkoxy ketones were prepared by a one-pot three-component reaction of aliphatic aldehydes, ketones, and alcohols catalyzed by l-proline. Steric effects on the reaction were studied with substituted ketones, aldehydes, and alcohols, and the results indicate that reactions employing methyl ketones, α-unsubstituted aliphatic aldehydes and methanol produce the β-alkoxy ketones in the best yields when l-proline is used as the catalyst. The reaction mechanism is discussed.

Key words

β-alkoxy ketones - aldehydes - alcohols - one-pot reaction - aldol reactions - Mannich addition

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References

<A NAME="RM02906SS-1">1</A> Kim BM. Williams SF. Masamune S. In Comprehensive Organic Synthesis Vol. 2: Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991. p.229-275

<A NAME="RM02906SS-2A">2a</A> Mukaiyama T. Hayashi M. Chem. Lett. 1974, 15

<A NAME="RM02906SS-2B">2b</A> Mukaiyama T. Angew. Chem., Int. Ed. Engl. 1977, 16: 817

<A NAME="RM02906SS-2C">2c</A> Murata S. Suzuki M. Noyori R. J. Am. Chem. Soc. 1980, 102: 3248

<A NAME="RM02906SS-2D">2d</A> Noyori R. Murata S. Suzuki M. Tetrahedron 1981, 37: 3899

<A NAME="RM02906SS-2E">2e</A> Murata S. Suzuki M. Noyori R. Tetrahedron 1988, 44: 4259

<A NAME="RM02906SS-2F">2f</A> Ishitani H. Iwamoto M. Tetrahedron Lett. 2003, 44: 299

<A NAME="RM02906SS-2G">2g</A> Cossy J. Lutz F. Alauze V. Meyer C. Synlett 2002, 45

<A NAME="RM02906SS-2H">2h</A> Trehan A. Vij A. Walia M. Kaur G. Verma RD. Trehan S. Tetrahedron Lett. 1993, 34: 7335

<A NAME="RM02906SS-2I">2i</A> Le Roux C. Ciliberti L. Laurent-Robert H. Laporterie A. Dubac J. Synlett 1998, 1249

<A NAME="RM02906SS-2J">2j</A> Ooi T. Tayama E. Takahashi M. Maruoka K. Tetrahedron Lett. 1997, 38: 7043

<A NAME="RM02906SS-2K">2k</A> Kamata M. Yokoyama Y. Karasawa N. Kato M. Hasegawa E. Tetrahedron Lett. 1996, 37: 3483

<A NAME="RM02906SS-2L">2l</A> Kamata M. Nagai S. Kato M. Hasegawa E. Tetrahedron Lett. 1996, 37: 7779

<A NAME="RM02906SS-2M">2m</A> Mukaiyama T. Kobayashi S. Murakami M. Chem. Lett. 1984, 1759

<A NAME="RM02906SS-2N">2n</A> Mukaiyama T. Iwakiri H. Chem. Lett. 1985, 1363

<A NAME="RM02906SS-2O">2o</A> Murakami M. Minamikawa H. Mukaiyama T. Chem. Lett. 1987, 1051

<A NAME="RM02906SS-2P">2p</A> Sakurai H. Sasaki K. Hosomi A. Bull. Chem. Soc. Jpn. 1983, 56: 3195

<A NAME="RM02906SS-2Q">2q</A> Hosomi A. Sakata Y. Sakurai H. Chem. Lett. 1983, 405

<A NAME="RM02906SS-2R">2r</A> Jung ME. Hogan KT. Tetrahedron Lett. 1988, 29: 6199

<A NAME="RM02906SS-2S">2s</A> Kawai M. Onaka M. Izumi Y. Bull. Chem. Soc. Jpn. 1988, 61: 1237

<A NAME="RM02906SS-3A">3a</A> Li L.-S. Das S. Sinha SC. Org. Lett. 2004, 6: 127

<A NAME="RM02906SS-3B">3b</A> Silvermann IT. Edington C. Elloitt JD. Johnson WS. J. Org. Chem. 1987, 52: 180

<A NAME="RM02906SS-4">4</A> Cullen AJ. Sammakia T. Org. Lett. 2004, 6: 3143

<A NAME="RM02906SS-5A">5a</A> Stewart IC. Bergman RG. Toste FD. J. Am. Chem. Soc. 2003, 125: 8696

<A NAME="RM02906SS-5B">5b</A> Kisanga PB. Ilankumaran P. Fetterly BM. Verkade JG. J. Org. Chem. 2002, 67: 3555

<A NAME="RM02906SS-6">6</A> Miller KJ. Kitagawa TT. Abu-Omar MM. Organometallics 2001, 20: 4403

<A NAME="RM02906SS-7">7</A> Kabashima H. Katou T. Hattorri H. Appl. Catal., A 2001, 214: 121

<A NAME="RM02906SS-8">8</A> Suga S. Suzuki S. Yamamoto A. Yoshida J.-I. J. Am. Chem. Soc. 2000, 122: 10244

<A NAME="RM02906SS-9">9</A> Masuyama Y. Kobayashi Y. Yanagi R. Kurusu Y. Chem. Lett. 1992, 2039

<A NAME="RM02906SS-10">10</A> Samanta S. Liu J. Dodda R. Zhao C.-G. Org. Lett. 2005, 7: 5321

<A NAME="RM02906SS-11A">11a</A> Cordova A. Notz W. Barbas CF. Chem. Commun. 2002, 3024

<A NAME="RM02906SS-11B">11b</A> Darbre T. Machuqueiro M. Chem. Commun. 2003, 1090

<A NAME="RM02906SS-11C">11c</A> Wu Y.-S. Shao W.-Y. Zheng C.-Q. Huang Z.-L. Cai J. Deng Q.-Y. Helv. Chim. Acta 2004, 87: 1377

<A NAME="RM02906SS-11D">11d</A> Peng Y.-Y. Ding Q.-P. Li Z. Wang PG. Cheng J.-P. Tetrahedron Lett. 2003, 44: 3871

Samanta, S.; Dodda, R.; Zhao, C.-G. unpublished results.

<A NAME="RM02906SS-12A">12a</A> Torii H. Nakadai M. Ishihara K. Saito S. Yamamoto H. Angew. Chem. Int. Ed. 2004, 43: 1983

<A NAME="RM02906SS-12B">12b</A> Cobb AJA. Shaw DM. Ley SV. Synlett 2004, 558

<A NAME="RM02906SS-13">13</A> List B. Lerner RA. Barbas CF. J. Am. Chem. Soc. 2000, 122: 2395

<A NAME="RM02906SS-14">14</A> List B. Pojarliev P. Castello C. Org. Lett. 2001, 3: 573