Dichlorotin oxide-catalyzed new direct functionalization of olefins: Synthesis of trans β-azidohydrins and 1,2-diols

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2415-2418

  Sakurada, Isao ^a   Yamasaki, Shingo ^a   Kanai, Motomu ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Dichlorotin oxide; Olefin; Trans substituted alcohol

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; AZIDE; BETA AZIDOHYDRIN; DICHLOROTIN OXIDE; METAL OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0034175703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00176-3     Document Type: Article

References (16)

1. trans 1,2-Diol synthesis from olefin (via dibenzoate): Wilson, C. V. In Organic Reactions; Adams, R., Ed.; John Wiley & Sons, Inc.: New York, 1957; Chapter 6, Vol. 9, p. 350.
2. Sakurada, I.; Yamasaki, S.; Iida, T.; Göttlich, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. in press.
3. 3, OCOR).
4. 2, 20 mL, 20 mmol) at 0°C under argon. After the mixture was stirred at rt for 2 h, volatiles (solvent, excess BTSP, chlorine, hexamethyldisiloxane) were evaporated in vacuo to afford dichlorotin oxide (2.4 g, 69%) as a white powder.
5. 3 (10 mL×3), evaporation of the solvent and purification by silica gel column chromatography (hexane-AcOEt 10:1) afforded 1 (74.0 mg, 52%).
6. The moderate isolated total yield of the products (azidohydrins or acetoxy alcohols+chlorohydrins) could be due to the formation of unknown by-products, whose structure determinations are under investigation.
7. 2O (pH 4.2), yield 67% (80:20)].
8. 2O (pH 4.2), yield 67% (80:20)].
9. 2O (pH 4.2), yield 67% (80:20)].
10. 2O (pH 4.2), yield 67% (80:20)].
11. The configuration of azidohydrins was determined by comparison with the literature data (compounds 1 and 2: Ref. 13; compounds 7, 9 and 11: Ref. 2) or by preparing authentic samples from corresponding epoxides.
12. Trimethylsilyl benzoate, trimethylsilyl o-nitrobenzoate, trimethylsilyl chloroacetate or trimethylsilyl dichloroacetate gave unsatisfactory results.
13. 2].
14. For a detailed discussion about the reaction mechanism, see Ref. 2.
15. Jackson, W. P. Synlett. 1990, 536.
16. Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602-2615.