Tetrahedron letters

Short stereocontrolled synthesis of trans and cis-tetrahydro-pyrazinoisoquinolinediones

JF González, E de la Cuesta, C Avendaño

Index: Gonzalez, Juan Francisco; De La Cuesta, Elena; Avendano, Carmen Tetrahedron Letters, 2003 , vol. 44, # 23 p. 4395 - 4398

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Citation Number: 20

Abstract

Addition of aldehyde dimethyl acetals (here acetaldehyde) to unisolated O-trimethylsilyl derivatives of 1-acetyl-3-arylmethylpiperazine-2, 5-diones (here 2, 5-dimethoxyphenyl), in the presence of TMSOTf as the catalyst, gave nearly quantitatively the corresponding N- methoxyalkyl derivatives which, under acidic treatment, gave in very good yield through a Pictet–Spengler-type reaction involving N-acyliminium cations (6S*, 11aR*)-2-acetyl-6- ...