Michael addition of selenoamides to α,β-unsaturated carbonyl compounds: Stereocontrolled synthesis of δ-oxo selenoamides and their reactivity

Organic Letters

Volumn 2, Issue 3, 2000, Pages 311-313

  Murai, Toshiaki ^a   Suzuki, Akiko ^a   Ezaka, Tatsuya ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

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Indexed keywords

EID: 0000944184     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990365s     Document Type: Article

References (24)

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19. 4 and concentrated in vacuo, and the residue was purified on column chromatography through silica gel using hexane/ether (10/1) as eluent to afford δ-oxo selenoamide 4c (0.268 g, 0.88 mmol) in 88% yield.
20. Wakefield, B. J. In Organolithium Methods; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: London, 1988; p 76.
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22. Product 6 was obtained in 80% yield with a purity higher than 90% after the workup. Attempts to purify the crude product through column chromatography failed and gave a complex mixture. Then, product 6 was purified by bulb-to-bulb distillation.
23. The stereochemistry of product 6 was determined by using a phase sensitive NOESY spectrum.
24. 4 and concentrated in vacuo, and the residue was purified on column chromatography through silica gel using hexane/ether (2/1) as eluent to afford δ-oxo selenoamide 9 (0.074 g, 0.23 mmol) in 45% yield.