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Trienamines: Their Key Role in Extended Organocatalysis for Diels-Alder Reactions

100%
Reboredo S., Parra A., Alemán J.
Asymmetric Catalysis
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2013
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vol. 1
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issue 1
EN
Activation via trienamine intermediates is a synthetically useful protocol for performing asymmetric Diels-Alder reactions controlled by a remote chiral catalyst (a secondary or primary amine). Key features underpinning this concept are the conformation towards the trienamine formation and also the use of highly electrophilic dienophiles. This cycloaddition reaction allows the application of asymmetric organocatalysis at a remote position, and the synthesis of complex molecules short synthetic sequences is possible.
2
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Solvent-controlled diastereoselectivity in tryptophan-catalyzed Mannich reactions

72%
Valero G., León C. M., Moyano A.
Asymmetric Catalysis
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2015
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vol. 2
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issue 1
EN
Solvent effects in the L-tryptophan-catalyzed Mannich reaction between hydroxyacetone and glyoxylate imines have been examined. The use of a DMSO/1-butanol (4:1 v/v) mixture as solvent at rt provided the expected Mannich adducts in good yields, high anti-diastereoselectivity (up to 10.3:1 anti/syn ratio) and excellent enantioselectivities (up to >99.9% ee for the anti isomer).
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