Rapid and Efficient Protocol for the Synthesis of 4-Chlorotetrahydropyrans Using Niobium(V) Chloride

J. S. Yadav; B. V. Subba Reddy; Manoj Kumar Gupta; Swapan Kumar Biswas

doi:10.1055/s-2004-831220

PAPER

Rapid and Efficient Protocol for the Synthesis of 4-Chlorotetrahydropyrans Using Niobium(V) Chloride

J. S. Yadav*, B. V. Subba Reddy, Manoj Kumar Gupta, Swapan Kumar Biswas
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;

Abstract

All articles of this category

Abstract

Aldehydes undergo a rapid coupling with 3-buten-1-ol utilizing 20 mol% of niobium(V) chloride to afford 4-chlorotetrahydropyran derivatives under extremely mild conditions within short reaction times in excellent yields with high selectivity. The similar halogenated tetrahydropyrans are also obtained using gallium(III) halides.

Keywords

Prins-cyclization - niobium(V) chloride - gallium(III) halides - halogenated tetrahydropyrans

Full Text

References

1 Prins HJ. Chem. Weekbl. 1919, 16: 1072

2 Adams DR. Bhatnagar SP. Synthesis 1977, 661

3 Chandrasekhar S. Reddy BVS. Synlett 1998, 851

4 Nicolaou KC. Sorensen EJ. Classics in Total Synthesis VCH; Weinheim: 1996.

5 Wei ZY. Li JS. Wang D. Chan T.-H. Tetrahedron Lett. 1987, 28: 3441

6 Perron F. Albizati KF. J. Org. Chem. 1987, 52: 4130

7 Wei ZY. Wang D. Li JS. Chan T.-H. J. Org. Chem. 1989, 54: 5768

8 Coppi L. Ricci A. Taddei M. J. Org. Chem. 1988, 53: 911

9 Yang J. Viswanathan GS. Li CJ. Tetrahedron Lett. 1999, 40: 1627

10 Yang J. Li C.-J. Synlett 1999, 717

11a Suzuki K. Hashimoto T. Maeta H. Matsumoto T. Synlett 1992, 125

11b Andrade CKZ. Azevedo NR. Oliveira GR. Synthesis 2002, 928

12 Matsuo J.-I. Kobayashi S. CHEMTRACTS 2000, 13: 431

13a Chatani N. Inoue H. Kotsuma T. Murai S. J. Am. Chem. Soc. 2002, 124: 10294

13b Inoue H. Chatani N. Murai S. J. Org. Chem. 2002, 67: 1414

13c Yamaguchi M. Tsukagoshi T. Arisawa M. J. Am. Chem. Soc. 1999, 121: 4074

13d Asao N. Asano T. Ohishi T. Yamamoto Y. J. Am. Chem. Soc. 2000, 122: 4817

14a Kobayashi K. Arisawa M. Yamaguchi M. J. Am. Chem. Soc. 2002, 124: 8528

14b Viswanathan GS. Wang M. Li C.-J. Angew. Chem. Int. Ed. 2002, 41: 2138

14c Viswanathan GS. Li C.-J. Synlett 2002, 1553

14d Viswanathan GS. Li C.-J. Tetrahedron Lett. 2002, 43: 1613

15a Andrade CKZ. Azevedo NR. Tetrahedron Lett. 2001, 42: 6473

15b Andrade CKZ. Oliveira GR. Tetrahedron Lett. 2002, 42: 6473

15c Andrade CKZ. Matos RAF. Synlett 2003, 1189

15d Andrews PC. Peatt AC. Raston CL. Tetrahedron Lett. 2004, 45: 243

15e Amemiya R. Fujii A. Yamaguchi M. Tetrahedron Lett. 2004, 45: 4333

16 Viswanathan GS. Yang J. Li C.-J. Org. Lett. 1999, 1: 993