Stereoselective Reduction of β-Hydroxy α-Ketoesters: A Concise Synthesis of anti-α,β-Dihydroxy Esters

Mingyi Liao; Wengang Yao; Jianbo Wang

doi:10.1055/s-2004-831210

PAPER

Stereoselective Reduction of β-Hydroxy α-Ketoesters: A Concise Synthesis of anti-α,β-Dihydroxy Esters

Mingyi Liao, Wengang Yao, Jianbo Wang*
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry, Peking University, Beijing 100871, P. R. of China
e-Mail: wangjb@pku.edu.cn;

Abstract

Alle Artikel dieser Rubrik

Abstract

A new synthetic route to anti-α,β-dihydroxy esters has been developed. The new method consists of three steps starting from an aldehyde: the nucleophilic condensation with ethyl diazoacetate, oxidation with dimethyldioxirane, and stereoselective reduction with NaBH₄.

Key words

diazo compounds - diols - nucleophilic addition - oxidation - reduction - diastereoselectivity

Volltext

Referenzen

References

1 For a review, see: Oishi T. Nakata T. Acc. Chem. Res. 1984, 17: 338

2a Stocker JH. Sidisuntlorn P. Benjamin BM. Collins CJ. J. Am. Chem. Soc. 1960, 82: 3913

2b Cram DJ. Wilson DR. J. Am. Chem. Soc. 1963, 85: 1245

2c Katzenellenbogen JA. Bowlus SB. J. Org. Chem. 1973, 38: 627

2d Bowlus SB. Katzenellenbogen JA. J. Org. Chem. 1974, 39: 3309

2e Tokuyama T. Shimada K. Uemura M. Daly JW. Tetrahedron Lett. 1982, 23: 2121

2f Overman LE. McCready RJ. Tetrahedron Lett. 1982, 23: 2355

2g Nakata T. Tanaka T. Oishi T. Tetrahedron Lett. 1983, 24: 2653

For reviews, see:

3a Schroder M. Chem. Rev. 1980, 80: 187

3b Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev. 1994, 94: 2483

4a Pearson WH. Cheng M.-C. J. Org. Chem. 1987, 52: 3176

4b Fujita M. Laine D. Ley SV. J. Chem. Soc., Perkin Trans. 1 1999, 1647

4c Andrus MB. Soma Sekhar BBV. Meredith EL. Dalley NK. Org. Lett. 2000, 2: 3035

4d Dixon DJ. Ley SV. Polara A. Sheppard T. Org. Lett. 2001, 3: 2749

5 anti-α,β-Dihydroxy esters were also synthesized through epoxidation of trans-α,β-unsaturated esters followed by hydrolysis and esterification. See: English J. Heywood DL. J. Am. Chem. Soc. 1955, 77: 4661

6 Ihmels H. Maggini M. Prato M. Scorrano G. Tetrahedron Lett. 1991, 32: 6215

7 Jiang N. Wang J. Tetrahedron Lett. 2002, 43: 1285 ; and references cited therein

8a Cram DJ. Abd Elhafez FA. J. Am. Chem. Soc. 1952, 74: 5828

8b Cram DJ. Wilson DR. J. Am. Chem. Soc. 1963, 85: 1245

9 Cherest M. Felkin H. Tetrahedron Lett. 1968, 28: 2205

10 Touzin AM. Tetrahedron Lett. 1975, 16: 1477