From Organocatalytic Cycloadditions to Asymmetric Higher-Order Cycloadditions

Karl Anker Jørgensen; K.N. Houk

doi:10.1002/9783527832217.ch17

From Organocatalytic Cycloadditions to Asymmetric Higher-Order Cycloadditions

Karl Anker Jørgensen, K.N. Houk

Institut for Kemi

Publikation: Bog/antologi/afhandling/rapport › Antologi › Forskning › peer review

Abstract

Controlling periselectivity and stereoselectivity of cycloadditions for systems having >6p-electrons has been a challenge ever since the introduction of the Woodward-Hoffmann rules. This chapter outlines how organocatalysis has been a key factor to control cycloadditions for reactions having >6p-electrons - termed higher-order cycloadditions. The application of aminocatalysis based on the application of chiral primary and secondary amines as catalysts for activating unsaturated ketones and aldehydes for [6+2]-, [6+4]-, [8+2]-, [10+2]-, [10+4]-, and [12+2] cycloadditions will be discussed. Focus is on how the combination of experimental and computational chemistry has paved the road for expanding the borders of cycloadditions. The impact of increasing the number of p-electrons beyond 6 in cycloadditions will be discussed.

Originalsprog	Engelsk

Udgivelsessted	Wiley Online Library
Forlag	Wiley-VCH
Vol/bind	1-2
Udgave	Volume 2
Antal sider	24
ISBN (Trykt)	9783527349074
ISBN (Elektronisk)	9783527832217
DOI	https://doi.org/10.1002/9783527832217.ch17
Status	Udgivet - 2023

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10.1002/9783527832217.ch17

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https://onlinelibrary.wiley.com/doi/chapter-epub/10.1002/9783527832217.ch17

Citationsformater

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AB - Controlling periselectivity and stereoselectivity of cycloadditions for systems having >6p-electrons has been a challenge ever since the introduction of the Woodward-Hoffmann rules. This chapter outlines how organocatalysis has been a key factor to control cycloadditions for reactions having >6p-electrons - termed higher-order cycloadditions. The application of aminocatalysis based on the application of chiral primary and secondary amines as catalysts for activating unsaturated ketones and aldehydes for [6+2]-, [6+4]-, [8+2]-, [10+2]-, [10+4]-, and [12+2] cycloadditions will be discussed. Focus is on how the combination of experimental and computational chemistry has paved the road for expanding the borders of cycloadditions. The impact of increasing the number of p-electrons beyond 6 in cycloadditions will be discussed.

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From Organocatalytic Cycloadditions to Asymmetric Higher-Order Cycloadditions

Abstract

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