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Synlett 2001; 2001(9): 1455-1457
DOI: 10.1055/s-2001-16784
DOI: 10.1055/s-2001-16784
letter
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Diastereoselective Synthesis of 4-Sila-3,4,4a,5-tetrahydro-2H-isoquinolin-1-ones through Intramolecular Diels-Alder Reaction of Chiral Silatrienes
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Publikationsverlauf
Publikationsdatum:
28. August 2001 (online)
![](https://www.thieme-connect.de/media/synlett/200109/lookinside/thumbnails/10.1055-s-2001-16784-1.jpg)
New Si-chiral N-2-silabut-3-enylpyran-2-one-6-carboxamides were prepared in four steps from dichloro(chloro-methyl)methylsilane. The thermal inverse electron demand intra-molecular Diels-Alder reaction of these compounds gave 4-sila-3,4,4a,5-tetrahydro-2H-isoquinolin-1-ones. Moderate diastereoselectivity was observed for a silatriene bearing a methyl and a cyclohexyl substituent on the chiral silicon atom. The intermediate tricyclic adduct of this reaction was also isolated.
Diels-Alder reactions - stereoselectivity - chiral silatrienes - 4-silatetrahydro-2H-isoquinolin-1-ones