Solid-Phase Synthesis of 3-Hydroxy-2-methylenealkanoates and Their Derivatives Using Polymer-Supported 2-(Phenylseleno)propanoate

Shou-Ri Sheng; Fang-Fang Huang; Shu-Ying Lin; Xiao-Ling Liu; Xian Huang

doi:10.1055/s-2007-966013

PAPER

Solid-Phase Synthesis of 3-Hydroxy-2-methylenealkanoates and Their Derivatives Using Polymer-Supported 2-(Phenylseleno)propanoate

Shou-Ri Sheng*^a, Fang-Fang Huang^a, Shu-Ying Lin^a, Xiao-Ling Liu^a, Xian Huang^a,b
^a Institutes of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330027, P. R. of China
Fax: +86(791)8506404; e-Mail: shengsr@jxnu.edu.cn;
^b Department of Chemistry, Zhejiang University, Hangzhou, 310028, P. R. of China

Abstract

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Abstract

A novel facile procedure for the solid-phase organic synthesis of 3-hydroxy-2-methylenealkanoates and their derivatives in good yields and with excellent purities using polymer-supported 2-(phenylseleno)propanoate is described.

Key words

solid-phase synthesis - 2-(phenylseleno)propanoate - oxidation - cleavage - 3-hydroxy-2-methylenealkanoates

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References

For recent reviews, see:

1a Shuttleworth SJ. Allin SM. Sharma PK. Synthesis 1997, 1217

1b Guillier F. Orain D. Bradley M. Chem. Rev. 2000, 100: 2091

1c Sammelson RE. Kurth MJ. Chem. Rev. 2001, 101: 137

1d Zhdankin VV. Stang PJ. Chem. Rev. 2002, 102: 2523

2a Hoffmann HMR. Rabe J. Angew. Chem., Int. Ed. Engl. 1985, 24: 94

2b Buchholz R. Hoffmann HMR. Helv. Chim. Acta 1991, 74: 1213

2c Basavaiah D. Bakthadoss M. Pandiaraju S. Chem. Commun. 1998, 1639

For review see:

3a Drewes SE. Roos GHP. Tetrahedron 1988, 44: 4653

3b Basavaiah D. Rao PD. Hyma RS. Tetrahedron 1996, 52: 8001

3c Ciganek E. Org. React. 1997, 51: 201

3d Marko IE. Giles GP. Hindley NJ. Tetrahedron 1997, 53: 1015

3e Langer P. Angew. Chem. Int. Ed. 2000, 39: 3049

3f Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev. 2003, 103: 811

For some recent examples for preparation of Morita-Baylis-Hillman adducts, see:

4a de Souza ROMA. Meireles BA. Aguiar LCS. Vasconcellos MLAA. Synthesis 2004, 1595

4b Krishna PR. Sekhar ER. Kannan SV. Synthesis 2004, 857

4c Zhao L.-J. He HS. Shi M. Toy PH. J. Comb. Chem. 2004, 6: 680

4d Luo SZ. Wang PG. Cheng J.-P. J. Org. Chem. 2004, 69: 555

4e Krishna PR. Lopinti KR. Kannan V. Tetrahedron Lett. 2004, 45: 7847

4f Krishna PR. Manjuvani A. Kannan V. Sharma GVM. Tetrahedron Lett. 2004, 45: 1183

4g Mi XL. Luo SZ. Cheng J.-P. J. Org. Chem. 2005, 70: 2338

4h Caumul P. Hailes HC. Tetrahedron Lett. 2005, 46: 8125

4i Pereira SI. Adrio J. Silva AMS. Carretero JC. J. Org. Chem. 2005, 70: 10175

4j Xue S. He L. Han K.-Z. Liu Y.-K. Guo Q.-X. Synlett 2005, 1247

4k Krishna PR. Manjuvani A. Sekhar EP. ARKIVOC 2005, (iii): 99

4l Lin Y.-S. Lin C.-Y. Liu C.-E. Tsai TYR. Tetrahedron 2006, 62: 872

5a Selenium Reagents and Intermediates in Organic Synthesis Paulmier C. Pergamon Press; Oxford: 1986.

5b Organoselenium Chemistry Liotta D. Wiley; New York: 1987.

5c Krief A. Comprehensive Organic Synthesis Trost BM. Fleming I. Pergamon; Oxford: 1991.

5d Back TG. Organoselenium Chemistry Oxford University Press; Oxford: 1999. p.173-191

5e Wirth T. Organoselenium Chemistry Springer; Berlin: 2000.

6a Krief A. Tetrahedron 1980, 36: 2531

6b Rollinson SW. Amos RA. Katzenellenbogen JA. J. Am. Chem. Soc. 1981, 103: 4114

7 Michels R. Kato M. Heitz W. Makromol. Chem. 1976, 177: 2311

8a Nicolaou KC. Pastor J. Barluenga S. Winssinger N. Chem. Commun. 1998, 1947

8b Ruhland T. Andersen K. Pedersen H. J. Org. Chem. 1998, 63: 9204

8c Yanada K. Fujita T. Yanada R. Synlett 1998, 971

8d Zaragoza F. Angew. Chem. Int. Ed. 2000, 39: 2077

8e Li Z. Kulkarni BA. Ganesan A. Biotechnol. Bioeng. 2001, 71: 104

8f Uehlin L. Wirth T. Org. Lett. 2001, 3: 2931

8g Fujita K.-I. Hashimoto S. Oishi A. Taguchi Y. Tetrahedron Lett. 2003, 44: 3793

8h Berlin S. Ericsson C. Engman L. J. Org. Chem. 2003, 68: 8386

8i Mogemark M. Gustafsson L. Bengtsson C. Elofsson M. Kihlberg J. Org. Lett. 2004, 6: 4885

8j Cohen RJ. Fox DL. Salvatore RN. J. Org. Chem. 2004, 69: 4265

9a Huang X. Sheng S.-R. Tetrahedron Lett. 2001, 42: 9035

9b Huang X. Sheng S.-R. J. Comb. Chem. 2003, 5: 805

9c Sheng S.-R. Liu X.-L. Wang X.-C. Xin Q. Song C.-S. Synthesis 2004, 2833

9d Sheng S.-R. Xin Q. Liu X.-L. Sun W.-K. Guo R. Huang X. Synthesis 2006, 2293

10 Yan B. Kumaravel G. Anjaria H. Wu A. Petter RC. Jewell CF. Wareing JR. J. Org. Chem. 1995, 60: 5736

11 Rollinson SW. Amos RA. Katzenellenbogen JA. J. Am. Chem. Soc. 1981, 103: 4114

12 Cai JX. Zhou ZH. Zhao GF. Tang CC. Org. Lett. 2002, 4: 4723

13 Foucaud A. Guemmout F. Bull. Soc. Chim. Fr. 1989, 403

14 Basavaiah D. Krishnamacharyulu M. Suguna Hyma R. Sarma PKS. Kumaragurubaran N. J. Org. Chem. 1999, 64: 1197

15 Drewes SE. Emslie ND. Field JS. Khan AA. Ramesar N. Tetrahedron: Asymmetry 1992, 3: 255