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Synthesis of a new versatile dienophile and its use in a highly diastereoselective Diels-Alder reaction

✍ Scribed by Jean-Luc Renaud; Corinne Aubert; Max Malacria

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
196 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

By using respectively one equivalent of the pmpafgyl zinc Mcolmlate and silylated pmpargyl bromide, the preparation of 2-me/hylenc-5-trimethylsilyl-pent-4-yn-l-ol was improved. This latter is the lm~'ta'sur of the com~pcmding aldehyde whkh was used for the first time as a dienophile in [4+2] reactions. The cycloadducts were obtained in very high yields and in a totally diasteremelective manner.

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