L-Proline-catalyzed enantioselective one-pot cross-Mannich reaction of aldehydes

Yujiro Hayashi, Tatsuya Urushima, Wataru Tsuboi, Mitsuru Shoji

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

This protocol describes a procedure for the synthesis of syn-β-amino α-substituted aldehydes, versatile intermediates in synthetic organic chemistry, via asymmetric, direct, one-pot, three-component, cross-Mannich reaction of two different aldehydes. The reaction consists of two steps; one is the formation of imine by the reaction of aldehyde and p-anisidine in the presence of Pro, and the second step is the enantioselective addition reaction of enamine generated from the other aldehyde and Pro with the imine generated in the first step. As the aldehyde easily racemizes, γ-amino alcohol was isolated and characterized after reduction. The yield and diastereo- and enantioselectivities are generally excellent. It will take approximately 26 h to complete the protocol: 0.5 h to set up the reaction, 20.5 h for the reaction and 5 h for the isolation and purification.

Original languageEnglish
Pages (from-to)113-118
Number of pages6
JournalNature Protocols
Volume2
Issue number1
DOIs
Publication statusPublished - 2007 Feb
Externally publishedYes

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Cross Reactions
Proline
Aldehydes
Imines
Organic Chemistry
Amino Alcohols
Addition reactions
Enantioselectivity
Purification

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

L-Proline-catalyzed enantioselective one-pot cross-Mannich reaction of aldehydes. / Hayashi, Yujiro; Urushima, Tatsuya; Tsuboi, Wataru; Shoji, Mitsuru.

In: Nature Protocols, Vol. 2, No. 1, 02.2007, p. 113-118.

Research output: Contribution to journalArticle

Hayashi, Yujiro ; Urushima, Tatsuya ; Tsuboi, Wataru ; Shoji, Mitsuru. / L-Proline-catalyzed enantioselective one-pot cross-Mannich reaction of aldehydes. In: Nature Protocols. 2007 ; Vol. 2, No. 1. pp. 113-118.
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