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The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles.
J Org Chem. 2003 Dec 12; 68(25):9624-34.JO

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.

Authors+Show Affiliations

Notz W
The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Tanaka F
No affiliation info available
Watanabe S
No affiliation info available
Chowdari NS
No affiliation info available
Turner JM
No affiliation info available
Thayumanavan R
No affiliation info available
Barbas CF
No affiliation info available

MeSH

AldehydesAmino AcidsAmino AlcoholsCatalysisDioxanesIminesLactamsMannich BasesModels, ChemicalProlinePyrrolidinesSolventsStereoisomerismStructure-Activity Relationship

Pub Type(s)

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

Language

eng

PubMed ID

14656087

Citation

Notz, Wolfgang, et al. "The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles." The Journal of Organic Chemistry, vol. 68, no. 25, 2003, pp. 9624-34.
Notz W, Tanaka F, Watanabe S, et al. The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles. J Org Chem. 2003;68(25):9624-34.
Notz, W., Tanaka, F., Watanabe, S., Chowdari, N. S., Turner, J. M., Thayumanavan, R., & Barbas, C. F. (2003). The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles. The Journal of Organic Chemistry, 68(25), 9624-34.
Notz W, et al. The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles. J Org Chem. 2003 Dec 12;68(25):9624-34. PubMed PMID: 14656087.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles. AU - Notz,Wolfgang, AU - Tanaka,Fujie, AU - Watanabe,Shin-Ichi, AU - Chowdari,Naidu S, AU - Turner,James M, AU - Thayumanavan,Rajeswari, AU - Barbas,Carlos F,3rd PY - 2003/12/6/pubmed PY - 2004/3/25/medline PY - 2003/12/6/entrez SP - 9624 EP - 34 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 25 N2 - 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. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/14656087/The_direct_organocatalytic_asymmetric_mannich_reaction:_unmodified_aldehydes_as_nucleophiles_ DB - PRIME DP - Unbound Medicine ER -