Work

Enantioselective Organo-SOMO Cascade Cycloadditions: A Rapid Approach to Molecular Complexity from Simple Aldehydes and Olefins

Year: 2010

Type: article

Abstract: A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja104313x

Authors: Nathan T. Jui, Esther C. Y. Lee, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, National Institute of General Medical Sciences

Awards: New Strategies in Metallaphotoredox Catalysis, G7747101108