Unknown

Dataset Information

0

Enantioselective organo-SOMO cycloadditions: a catalytic approach to complex pyrrolidines from olefins and aldehydes.


ABSTRACT: A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnish a cationic intermediate which is vulnerable to nucleophilic addition of a tethered amine group. A range of olefins, including styrenes and dienes, are shown to provide stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.

SUBMITTER: Jui NT 

PROVIDER: S-EPMC3408613 | BioStudies | 2012-01-01

REPOSITORIES: biostudies

Similar Datasets

2010-01-01 | S-EPMC3041020 | BioStudies
2010-01-01 | S-EPMC2880463 | BioStudies
2011-01-01 | S-EPMC3474369 | BioStudies
2009-01-01 | S-EPMC2758563 | BioStudies
2010-01-01 | S-EPMC2862978 | BioStudies
2018-01-01 | S-EPMC5767877 | BioStudies
2020-01-01 | S-EPMC7496861 | BioStudies
2018-01-01 | S-EPMC6092015 | BioStudies
1000-01-01 | S-EPMC4011570 | BioStudies
2018-01-01 | S-EPMC6687088 | BioStudies