The Preparation of Enantiomerically Pure 3,4-Epoxy-1-butene and 3-Butene-1,2-diol

Neil W. Boaz; Stephen N. Falling; Mary K. Moore

doi:10.1055/s-2005-869867

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Synlett 2005(10): 1615-1617
DOI: 10.1055/s-2005-869867

LETTER

The Preparation of Enantiomerically Pure 3,4-Epoxy-1-butene and 3-Butene-1,2-diol

Neil W. Boaz*, Stephen N. Falling, Mary K. Moore
Research Laboratories, Eastman Chemical Company, P.O. Box 1972, Kingsport, TN 37662, USA
Fax: +1(423)2247582; e-Mail: nwboaz@eastman.com;

Further Information

Publication History

Received 11 March 2005
Publication Date:
07 June 2005 (online)

Abstract
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Abstract

Single enantiomer 2-hydroxy-3-butenyl tosylate is a key precursor for single enantiomer 3,4-epoxy-1-butene and 3-butene-1,2-diol. The epoxide results from ring-closure of the hydroxy-tosylate while the diol is obtained through the intermediacy of the corresponding cyclic carbonate. This latter sequence avoids the loss of enantiomeric purity observed through direct hydrolysis.

Key words

epoxides - asymmetric synthesis - chirality - diols - nucleophiles

References

1a Kozikowski AP. Ghosh AK. J. Am. Chem. Soc. 1982, 104: 5788

Crossref Google Scholar
1b Kozikowski AP. Ghosh AK. J. Org. Chem. 1984, 49: 2762

Crossref Google Scholar
2 Walkup RD. Cunningham RT. Tetrahedron Lett. 1987, 28: 4019

Crossref Google Scholar
3a Rama Rao AV. Reddy ER. Joshi BV. Yadav JS. Tetrahedron Lett. 1987, 28: 6497

Crossref Google Scholar
3b Rama Rao AV. Bose DS. Gurjar MK. Ravindranathan T. Tetrahedron 1989, 45: 7031

Crossref Google Scholar
4 Gurjar MK. Devi NR. Tetrahedron: Asymmetry 1994, 5: 755

Crossref Google Scholar
5 Bergmeier SC. Stanchina DM. J. Org. Chem. 1999, 64: 2852

Crossref Google Scholar
6 Maeda M. Okazaki F. Murayama M. Tachibana Y. Aoyagi Y. Ohta A. Chem. Pharm. Bull. 1997, 45: 962

Crossref Google Scholar
7 Ohgiya T. Nishiyama S. Heterocycles 2004, 63: 2349

Crossref Google Scholar
8a Baer E. Fischer HO. J. Biol. Chem. 1939, 128: 463

Crossref Google Scholar
8b Crawford RJ. Lutener SB. Cockcroft RD. Can. J. Chem. 1976, 54: 3364

Crossref Google Scholar
9a Jung ME. Shaw TJ. J. Am. Chem. Soc. 1980, 102: 6304

Article in Thieme Connect Google Scholar
9b Marco JL. Rodriguez B. Tetrahedron Lett. 1988, 29: 1997

Article in Thieme Connect Google Scholar
9c Takano S. Numata H. Ogasawara K. Heterocycles 1982, 19: 327

Article in Thieme Connect Google Scholar
9d Hubschwerlen C. Synthesis 1986, 962

Article in Thieme Connect Google Scholar
10 Howes DA. Brookes MH. Coates D. Golding BT. Hudson AT. J. Chem. Res., Synop. 1983, 9 ; J. Chem. Res., Miniprint 1983, 217

Google Scholar
11a Tokunaga M. Larrow JF. Kakiuchi F. Jacobsen EN. Science 1997, 277: 936

Crossref PubMed Google Scholar
11b Schaus SE. Brandes BD. Larrow JF. Tokunaga M. Hansen KB. Gould AE. Furrow ME. Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 1307

Crossref PubMed Google Scholar
12a Trost BM. McEachern EJ. J. Am. Chem. Soc. 1999, 121: 8649

Crossref Google Scholar
12b Cheeseman N. Fox M. Jackson M. Lennon IC. Meek G. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5396

Crossref Google Scholar
13 Boaz NW. Zimmerman RL. Tetrahedron: Asymmetry 1994, 5: 153

Crossref Google Scholar
14 Neagu C. Hase T. Tetrahedron Lett. 1993, 34: 1629

Crossref Google Scholar
15 Boaz NW. Tetrahedron: Asymmetry 1995, 6: 15

Crossref Google Scholar
16a Cardillo G. Orena M. Porzi G. Sandri S. Synthesis 1981, 793

Crossref Google Scholar
16b Myers AG. Widdowson KL. Tetrahedron Lett. 1988, 29: 6389

Crossref Google Scholar
17 Boaz NW. inventors; US Patent No. 5312950.