One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids

Luca Deiana; Gui Ling Zhao; Pawel Dziedzic; Ramon Rios; Jan Vesely; Jesper Ekström; Armando Córdova

doi:10.1016/j.tetlet.2009.10.130

One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids

Luca Deiana
, Gui Ling Zhao
, Pawel Dziedzic
, Ramon Rios
, Jan Vesely
, Jesper Ekström
, Armando Córdova

Chemistry

Arrhenius Laboratory

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97->99% ee.

Original language	British English
Pages (from-to)	234-237
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2009.10.130
State	Published - 13 Jan 2010

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title = "One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids",

abstract = "A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97->99\% ee.",

author = "Luca Deiana and Zhao, \{Gui Ling\} and Pawel Dziedzic and Ramon Rios and Jan Vesely and Jesper Ekstr{\"o}m and Armando C{\'o}rdova",

note = "Funding Information: We gratefully acknowledge the Swedish National Research Council and Carl-Trygger Foundation for financial support. ",

year = "2010",

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doi = "10.1016/j.tetlet.2009.10.130",

language = "British English",

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T1 - One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones

T2 - asymmetric synthesis of β-amino aldehydes and β-amino acids

AU - Deiana, Luca

AU - Zhao, Gui Ling

AU - Dziedzic, Pawel

AU - Rios, Ramon

AU - Vesely, Jan

AU - Ekström, Jesper

AU - Córdova, Armando

N1 - Funding Information: We gratefully acknowledge the Swedish National Research Council and Carl-Trygger Foundation for financial support.

PY - 2010/1/13

Y1 - 2010/1/13

N2 - A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97->99% ee.

AB - A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97->99% ee.

UR - https://www.scopus.com/pages/publications/71049138987

U2 - 10.1016/j.tetlet.2009.10.130

DO - 10.1016/j.tetlet.2009.10.130

M3 - Article

AN - SCOPUS:71049138987

SN - 0040-4039

VL - 51

SP - 234

EP - 237

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids

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