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Synlett 2001; 2001(9): 1455-1457
DOI: 10.1055/s-2001-16784
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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

Paulo J. Coelho* , Luis Blanco
  • *Laboratoire des Carbocycles (Associé au CNRS), Institut de Chimie Moléculaire d'Orsay, Bât 420, Université de Paris-Sud, 91405 Orsay, France; Fax + 351-259-350480; E-mail: Pcoelho@marao.utad.pt
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Publication History

Publication Date:
28 August 2001 (online)

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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