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A Highly Enantioselective Route to Either Enantiomer of Both α- and β-Amino Acid Derivatives
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Section:Abstract
This report describes the unprecedented use of unmodified aldehydes as donors in a catalytic asymmetric Mannich-type reaction. The proline-catalyzed reaction of N-PMP-protected α-imino ethyl glyoxylate with unmodified aliphatic aldehydes provided a general and very mild entry to either enantiomer of β-amino and α-amino acids and derivatives in high yield and stereoselectivity. Six of the seven aldehydes studied yielded products with ee values of 99% or greater. The diastereoselectivity of the reaction increased with the bulkiness of the substituents of the aldehyde donor in the order R = Me < Et < i-Pr < n-Pent. In five of the cases studied, excellent syn stereoselectivities were achieved. In addition, the corresponding chiral β-amino aldehyde adducts can be readily converted to the corresponding amino acid derivatives. Most significantly, this approach provides facile access to substituted β-lactams.
Citing Articles
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This article has been cited by 74 ACS Journal articles (5 most recent appear below).
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A Straightforward Three-Component Synthesis of α-Amino Esters Containing a Phenylalanine or a Phenylglycine Scaffold
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An Organocatalyzed Enantioselective Synthesis of (2S,3R,4S)-4-Hydroxyisoleucine and Its Stereoisomers
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Enantioselective Organocatalytic Mannich Reactions with Autocatalysts and Their Mimics
Xinbo Wang, Yongbo Zhang, Haibo Tan, Yanchao Wang, Peng Han and David Zhigang WangThe Journal of Organic Chemistry2010 75 (7), 2403-2406Enantioselective Organocatalytic Mannich Reactions with Autocatalysts and Their Mimics
Xinbo Wang, Yongbo Zhang, Haibo Tan, Yanchao Wang, Peng Han and David Zhigang WangThe Journal of Organic Chemistry2010 75 (7), 2403-2406The Mannich reactions previously extensively investigated with organocatalysis of l-proline and other related small molecules were reinvestigated with detailed stereochemical analysis of their autocatalysis pathways, through employment of both the ...
Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with in situ Generated N-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea
Haile Zhang, Salahuddin Syed and Carlos F. Barbas, IIIOrganic Letters2010 12 (4), 708-711Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with in situ Generated N-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea
Haile Zhang, Salahuddin Syed and Carlos F. Barbas, IIIOrganic Letters2010 12 (4), 708-711Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable α-amido sulfones. Catalysis mediated by a cinchona alkaloid ...
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History
- Published In Issue March 06, 2002
- Received December 20, 2001
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