Synlett 2001; 2001(9): 1455-1457
DOI: 10.1055/s-2001-16784
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
28 August 2001 (online)

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.