Hetero [4 + 2] cycloadditions of (trialkylsilyl)vinylketenes. Synthesis of α,β-unsaturated δ-valerolactones and -lactams

Organic Letters

Volumn 1, Issue 4, 1999, Pages 641-644

  Bennett, Dawn M ^a   Okamoto, Iwao ^a   Danheiser, Rick L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; ORGANOSILICON DERIVATIVE; PYRIDONE DERIVATIVE; PYRONE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; KETONES; ORGANOSILICON COMPOUNDS; PYRIDONES; PYRONES;

EID: 0033606865     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9907217     Document Type: Article

References (29)

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22. 13C NMR, and elemental analyses were fully consistent with the assigned structures (see Supporting Information).
23. 4NF in THF (25 °C, 30 min) led to a complex mixture of products.
24. For the synthesis and chemistry of N-silyl imines, see: Panunzio, M.; Zarontonello, P. Org. Process Res. Dev. 1998, 1, 49.
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27. 1H NMR difference NOE experiments.
28. For a review on [2 + 2] cycloadditions of imines and ketenes, see: Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 295-368.
29. The [2 + 2] cycloaddition of N-silyl imines with silylketenes has not been reported previously, although Staudinger reactions of silyl imines with ketenes (generated by dehydrochlorination of acyl chlorides) have been studied extensively by Panunzio and co-workers. See: Bacchi, S.; Bongini, A.; Panunzio, M.; Villa, M. Synlett 1998, 843 and references therein.