O -nitroso aldol synthesis: Catalytic enantioselective route to α-aminooxy carbonyl compounds via enamine intermediate
- 5 April 2004
- journal article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 101 (15), 5374-5378
- https://doi.org/10.1073/pnas.0307785101
Abstract
The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Brønsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.Keywords
This publication has 42 references indexed in Scilit:
- The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as NucleophilesThe Journal of Organic Chemistry, 2003
- Structure–Nucleophilicity Relationships for EnaminesChemistry – A European Journal, 2003
- Organocatalytic Asymmetric Conjugate Addition of Nitroalkanes to α,β-Unsaturated Enones Using Novel Imidazoline CatalystsThe Journal of Organic Chemistry, 2002
- Tandem Enamine Michael Additions to 4-(Mesyloxy)cyclopentenones: Bridged Tricyclic Skeletons via a Net [3 + 2] Construction1Journal of the American Chemical Society, 1997
- Synthesis and biological activity of carboxylic acid replacement analogs of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-prolineJournal of Medicinal Chemistry, 1985
- New Crossed Aldol Reaction. Reaction of Enamines with Aldehydes Activated by Lewis AcidsBulletin of the Chemical Society of Japan, 1985
- Alkylation of Ketones and Aldehydes via their Nitrogen DerivativesSynthesis, 1983
- Enantioselective Catalytic Hydrogenation of α-Acetylaminoacrylic AcidsSynthesis, 1981
- N-Nitrosoenamines, versatile new synthesis intermediatesThe Journal of Organic Chemistry, 1980
- The Enamine Alkylation and Acylation of Carbonyl CompoundsJournal of the American Chemical Society, 1963