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Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines.
Nat Protoc. 2007; 2(8):1937-42.NP

Abstract

This protocol describes a procedure for the synthesis of alpha, beta-branched-b-amino aldehydes via Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-tert-butoxycarbonyl-imines. The crystalline beta-amino aldehydes are formed in good yields and extremely high levels of diastereo- and enantioselectivities without the need for chromatographic purification and are readily oxidized to the corresponding beta-amino acids. The protocol can be completed in approximately 14 h on small scales or up to 30 h on larger scales.

Authors+Show Affiliations

Yang JW
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany.
Stadler M
No affiliation info available
List B
No affiliation info available

MeSH

AcetonitrilesAldehydesBenzaldehydesCatalysisChemistry, OrganicFormic Acid EstersIminesProline

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17703205

Citation

Yang, Jung Woon, et al. "Practical Proline-catalyzed Asymmetric Mannich Reaction of Aldehydes With N-Boc-imines." Nature Protocols, vol. 2, no. 8, 2007, pp. 1937-42.
Yang JW, Stadler M, List B. Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines. Nat Protoc. 2007;2(8):1937-42.
Yang, J. W., Stadler, M., & List, B. (2007). Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines. Nature Protocols, 2(8), 1937-42.
Yang JW, Stadler M, List B. Practical Proline-catalyzed Asymmetric Mannich Reaction of Aldehydes With N-Boc-imines. Nat Protoc. 2007;2(8):1937-42. PubMed PMID: 17703205.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines. AU - Yang,Jung Woon, AU - Stadler,Michael, AU - List,Benjamin, PY - 2007/8/19/pubmed PY - 2007/12/7/medline PY - 2007/8/19/entrez SP - 1937 EP - 42 JF - Nature protocols JO - Nat Protoc VL - 2 IS - 8 N2 - This protocol describes a procedure for the synthesis of alpha, beta-branched-b-amino aldehydes via Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-tert-butoxycarbonyl-imines. The crystalline beta-amino aldehydes are formed in good yields and extremely high levels of diastereo- and enantioselectivities without the need for chromatographic purification and are readily oxidized to the corresponding beta-amino acids. The protocol can be completed in approximately 14 h on small scales or up to 30 h on larger scales. SN - 1750-2799 UR - https://www.unboundmedicine.com/medline/citation/17703205/Practical_Proline_catalyzed_asymmetric_Mannich_reaction_of_aldehydes_with_N_Boc_imines_ L2 - https://doi.org/10.1038/nprot.2007.272 DB - PRIME DP - Unbound Medicine ER -