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A novel domino (4+2)/(4+2)/(3+2) cycloaddition reaction leading to highly functionalized polycyclic nitroso acetals

✍ Scribed by Leon W.A van Berkom; George J.T Kuster; Faysal Kalmoua; René de Gelder; Hans W Scheeren

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 190 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01123-7

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✦ Synopsis

2-Methoxybuta-1,3-diene reacts under high pressure conditions in a one-pot domino (4+2)/(4+2)/(3+2) cycloaddition reaction with a dienophile, b-nitrostyrene and a dipolarophile to give tri, tetra and pentacyclic nitroso acetals. In this novel domino reaction up to six bonds and up to eight stereogenic centers are created in one step in good yield and good stereoselectivity.

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