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Direct-type catalytic three-component mannich reactions leading to an efficient synthesis of alpha,beta-diamino acid derivatives.
Org Lett. 2006 Aug 03; 8(16):3533-6.OL

Abstract

[reaction: see text] The first example of the Lewis acid-catalyzed three-component direct-type Mannich reaction of simple aromatic and enolizable aliphatic aldehydes, secondary amines, and glycine derivatives is described. The procedure is highly atom economical and can be performed in a simple one-pot operation under mild conditions to afford a wide variety of synthetically important anti-alpha,beta-diamino ester derivatives in high yields with high diastereoselectivities.

Authors+Show Affiliations

Salter MM
Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kobayashi J
No affiliation info available
Shimizu Y
No affiliation info available
Kobayashi S
No affiliation info available

MeSH

AldehydesAminesAmino AcidsCatalysisEstersGlycineMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

16869653

Citation

Salter, Matthew M., et al. "Direct-type Catalytic Three-component Mannich Reactions Leading to an Efficient Synthesis of Alpha,beta-diamino Acid Derivatives." Organic Letters, vol. 8, no. 16, 2006, pp. 3533-6.
Salter MM, Kobayashi J, Shimizu Y, et al. Direct-type catalytic three-component mannich reactions leading to an efficient synthesis of alpha,beta-diamino acid derivatives. Org Lett. 2006;8(16):3533-6.
Salter, M. M., Kobayashi, J., Shimizu, Y., & Kobayashi, S. (2006). Direct-type catalytic three-component mannich reactions leading to an efficient synthesis of alpha,beta-diamino acid derivatives. Organic Letters, 8(16), 3533-6.
Salter MM, et al. Direct-type Catalytic Three-component Mannich Reactions Leading to an Efficient Synthesis of Alpha,beta-diamino Acid Derivatives. Org Lett. 2006 Aug 3;8(16):3533-6. PubMed PMID: 16869653.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct-type catalytic three-component mannich reactions leading to an efficient synthesis of alpha,beta-diamino acid derivatives. AU - Salter,Matthew M, AU - Kobayashi,Jun, AU - Shimizu,Yusuke, AU - Kobayashi,Shu, PY - 2006/7/28/pubmed PY - 2007/6/7/medline PY - 2006/7/28/entrez SP - 3533 EP - 6 JF - Organic letters JO - Org Lett VL - 8 IS - 16 N2 - [reaction: see text] The first example of the Lewis acid-catalyzed three-component direct-type Mannich reaction of simple aromatic and enolizable aliphatic aldehydes, secondary amines, and glycine derivatives is described. The procedure is highly atom economical and can be performed in a simple one-pot operation under mild conditions to afford a wide variety of synthetically important anti-alpha,beta-diamino ester derivatives in high yields with high diastereoselectivities. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16869653/Direct_type_catalytic_three_component_mannich_reactions_leading_to_an_efficient_synthesis_of_alphabeta_diamino_acid_derivatives_ L2 - https://doi.org/10.1021/ol0613012 DB - PRIME DP - Unbound Medicine ER -
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