Highly stereoselective coupling reaction of acrolein or vinyl ketone with aldehydes

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1383-1385

  Uehira, Shigeki ^a   Han, Zhenfu ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000000271     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990934w     Document Type: Article

References (29)

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15. 2 (3 mL) at 0°C. After being stirred for 10 min at 0°C, a resulting dark-red solution was cooled to -78°C, and 2-methylpropanal (3.0 mmol) and acrolein (1.0 mmol) were added. The mixture was stirred for 30 min at -78°C, and then the whole mixture was poured into saturated aqueous ammonium chloride. Extractive workup and purification by silica gel column chromatography afforded 4-hydroxy-2,6-diisopropyl-5-iodomethyl-1,3-dioxane (2a, 0.22 g) in 68% yield.
16. 3SnH provided 2,4-dimethyl-1,3-pentanediol as a single isomer (>99/1). This product was identical with authentic syn-diol. The assignment of relative stereochemistry of another isopropyl group was based on NOE experiment. The anomeric stereocenter was assumed taking account of the anomeric effect.
17. Some attempts to obtain 3-hydroxyaldehyde 1 as a major product were not successful.
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28. 3SiOTf.
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