✦ LIBER ✦

Unexpectedly high diastereomeric induction in the diels-alder reaction of quinones with chiral aryl containing 1-alkoxy-3-trimethylsilyloxybuta-1,3-dienes.

✍ Scribed by J.F.M de Bie; G.P.F van Strijdonck; J.P Seerden; G Beurskens; J.W Scheeren

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 298 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97288-5

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✦ Synopsis

Absaact: Chiral l-~oxy-3-aimethylsilyloxybuta-13-dimes induce a high diastereomezic e.xcess in the cycloadditiott with quinottes when the chid alkoxy group is of the type OCH(CH3)R with R = aryl. Also for R = vinyl, CH$ICH3 dte found induction is higkr dtan that observed for R = tert. butyl. The highest diastereomuic excess (235%) was achieved in the cychddition of l-[l-@-methxypheny&ethoxy]-3aimethylsilyloxybuta-1.3diene with bcnwquinone. An explanation is givm based on the assumption that the R substituent is strongly enlarged in size by complexation with the wed quinones.

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