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An acyliminium ion approach towards the synthesis of β-substituted 3,4-dihydroisoquinolone propionates

✍ Scribed by Matthew J Fisher; Bruce P Gunn; Suzane Um; Joseph A Jakubowski

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
229 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

A variety of ¢-methoxy amides were prepared either by selective reduction of the exocyclic carbonyl of a 2-acyl-3,4dihydroisoquinolone and subsequent trapping of the resultant tt-hydroxy amide with acidic methanol or by reacting the sodium salt of 3,4-dihydroisoquinolone with a functionalized ct-chloro ether. These intermediates were reacted with l-tert-butoxy-l-tertbutyldimethylsiloxy ethene in the presence of BF3.Et20 providing access to I~-substituted isoquinolone propionates in good yield.

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