Asymmetric Brønsted Acid Catalyzed Cycloadditions of ortho-Quinone Methides and Related Compounds

Dedicated to Prof. Dr. Lutz F. Tietze with deep respect and admiration on the occasion of his 80^th birthday

Abstract

This review summarizes recent developments in the area of Brønsted acid catalyzed, enantioselective cycloadditions of ortho-quinone methides, ortho-quinone methide imines as well as heterocyclic indole- and pyrrole-based methides. In a straightforward and single-step transformation complex polycyclic N- and O-heterocyclic scaffolds are accessible, with typically good yields and excellent stereocontrol, from simple benzyl and heterobenzyl alcohols upon acid-catalyzed dehydration. The transient precursors are hydrogen-bonded to a chiral Brønsted acid which controls the enantioselectivity of the process.

1 Introduction

2 Cycloadditions of ortho-Quinone Methides

2.1 Brønsted Acid Catalyzed Processes

2.2 Cooperative Brønsted Acid/Transition-Metal-Catalyzed Processes

3 Cycloadditions of ortho-Quinone Methide Imines

4 Cycloadditions of Indolyl-3-methides

5 Cycloadditions of Indolyl-2-methides

5.1 Brønsted Acid Catalyzed Processes

5.2 Cooperative Brønsted Acid/Transition-Metal-Catalyzed Processes

6 Cycloadditions of Pyrrolyl-2-methides

7 Cycloadditions of Pyrrolyl-3-methides

8 Conclusions

Key words

cycloaddition - heterocycles - indoles - pyrroles - chromans - enantioselectivity - Brønsted acid catalysis

Publication History

Received: 24 January 2022

Accepted after revision: 24 February 2022

Accepted Manuscript online:
24 February 2022

Article published online:
21 April 2022

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