The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles
Top Cited Papers
- 13 November 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (25) , 9624-9634
- https://doi.org/10.1021/jo0347359
Abstract
The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized alpha- and beta-amino acids, beta-lactams, and amino alcohols.Keywords
This publication has 78 references indexed in Scilit:
- Catalytic, Enantioselective Alkylation of α-Imino Esters: The Synthesis of Nonnatural α-Amino Acid DerivativesJournal of the American Chemical Society, 2001
- Mechanism of Palladium Complex-Catalyzed Enantioselective Mannich-Type Reaction: Characterization of A Novel Binuclear Palladium Enolate ComplexJournal of the American Chemical Society, 1999
- Catalytic, Enantioselective Alkylations of N,O-AcetalsThe Journal of Organic Chemistry, 1999
- Catalytic asymmetric reaction of lithium ester enolates with iminesChemical Communications, 1999
- Unexpected Catalytic Behavior of Chiral Bisoxazoline in Asymmetric Reaction of Lithium Ester Enolate with Imine.CHEMICAL & PHARMACEUTICAL BULLETIN, 1999
- Regio‐ and Diastereoselective Synthesis of β‐Amino Ketones by Addition of Imines to Iminium SaltsAngewandte Chemie International Edition in English, 1996
- A Large-Scale Preparation of (3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine and Its Analogs from L-Aspartic Acid.CHEMICAL & PHARMACEUTICAL BULLETIN, 1996
- An Efficient Synthesis of (S)-(+)-Ethyl β-Amino-3-pyridinepropanoate Using Enantiopure SulfiniminesThe Journal of Organic Chemistry, 1996
- Stereokontrollierte Synthesen von Mannich‐Basen und γ‐AminoalkoholenEuropean Journal of Organic Chemistry, 1992
- Synthesen mit Isoxazolinen, 6. Asymmetrische Induktion bei der Reduktion von 2‐Isoxazolinen zu γ‐Aminoalkoholen mit zwei und drei benachbarten Stereozentren2,3)European Journal of Organic Chemistry, 1980