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

Org Lett

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

Published: October 2022


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Article Abstract

The asymmetric catalytic [4 + 2] cycloannulation of -aminophenyl -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 -aminophenyl -QMs. This reaction exhibits excellent functional group tolerance. Excellent yields, exclusive diastereoselectivities, and high enantioselectivities were obtained in this efficient organocatalytic reaction.

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http://dx.doi.org/10.1021/acs.orglett.2c02874DOI Listing

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

Org Lett

October 2022

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

The asymmetric catalytic [4 + 2] cycloannulation of -aminophenyl -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 -aminophenyl -QMs. This reaction exhibits excellent functional group tolerance.

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