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Organocatalytic Asymmetric Synthesis of Tetrahydroquinolines from ortho-Aminophenyl para-Quinone Methides.

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The asymmetric catalytic [4 + 2] cycloannulation of ortho-aminophenyl p-QMs with different types of alkenes for the construction of tetrahydroquinolines containing three contiguous stereogenic centers was developed. This is the… Click to show full abstract

The asymmetric catalytic [4 + 2] cycloannulation of ortho-aminophenyl p-QMs with different types of alkenes for the construction of tetrahydroquinolines containing three contiguous stereogenic centers was developed. This is the first example of catalytic asymmetric cycloannulation of ortho-aminophenyl p-QMs. This reaction exhibits excellent functional group tolerance. Excellent yields, exclusive diastereoselectivities, and high enantioselectivities were obtained in this efficient organocatalytic reaction.

Keywords: synthesis tetrahydroquinolines; ortho aminophenyl; organocatalytic asymmetric; aminophenyl para; asymmetric synthesis; tetrahydroquinolines ortho

Journal Title: Organic letters
Year Published: 2022

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