Catalysis of highly stereoselective Mannich-type reactions of ketones with Î±-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids

Wei Wang; Jian Wang; Hao Li

doi:10.1016/j.tetlet.2004.08.032

Catalysis of highly stereoselective Mannich-type reactions of ketones with Î±-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids

Wei Wang
, Jian Wang
, Hao Li

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

90 Scopus citations

Abstract

The novel pyrrolidine-sulfonamide I has been prepared and used successfully to catalyze Mannich-type reactions between ketones and α-imino esters. The process is used to efficiently synthesize functionalized α-amino acid derivatives with excellent levels of regio-, diastereo-, and enantio-selectivity.

Original language	English (US)
Pages (from-to)	7243-7246
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2004.08.032
State	Published - Sep 20 2004
Externally published	Yes

Keywords

Amino acids
Asymmetric catalysis
Ketones
Mannich reaction
Pyrrolidine-sulfonamide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2004.08.032

Cite this

@article{c9713b213aa646abaab5dfd8ab897da4,

title = "Catalysis of highly stereoselective Mannich-type reactions of ketones with {\^I}±-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids",

abstract = "The novel pyrrolidine-sulfonamide I has been prepared and used successfully to catalyze Mannich-type reactions between ketones and α-imino esters. The process is used to efficiently synthesize functionalized α-amino acid derivatives with excellent levels of regio-, diastereo-, and enantio-selectivity.",

keywords = "Amino acids, Asymmetric catalysis, Ketones, Mannich reaction, Pyrrolidine-sulfonamide",

author = "Wei Wang and Jian Wang and Hao Li",

year = "2004",

month = sep,

day = "20",

doi = "10.1016/j.tetlet.2004.08.032",

language = "English (US)",

volume = "45",

pages = "7243--7246",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "39",

}

TY - JOUR

T1 - Catalysis of highly stereoselective Mannich-type reactions of ketones with Î±-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids

AU - Wang, Wei

AU - Wang, Jian

AU - Li, Hao

PY - 2004/9/20

Y1 - 2004/9/20

N2 - The novel pyrrolidine-sulfonamide I has been prepared and used successfully to catalyze Mannich-type reactions between ketones and α-imino esters. The process is used to efficiently synthesize functionalized α-amino acid derivatives with excellent levels of regio-, diastereo-, and enantio-selectivity.

AB - The novel pyrrolidine-sulfonamide I has been prepared and used successfully to catalyze Mannich-type reactions between ketones and α-imino esters. The process is used to efficiently synthesize functionalized α-amino acid derivatives with excellent levels of regio-, diastereo-, and enantio-selectivity.

KW - Amino acids

KW - Asymmetric catalysis

KW - Ketones

KW - Mannich reaction

KW - Pyrrolidine-sulfonamide

UR - https://www.scopus.com/pages/publications/4444276557

UR - https://www.scopus.com/pages/publications/4444276557#tab=citedBy

U2 - 10.1016/j.tetlet.2004.08.032

DO - 10.1016/j.tetlet.2004.08.032

M3 - Article

AN - SCOPUS:4444276557

SN - 0040-4039

VL - 45

SP - 7243

EP - 7246

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Catalysis of highly stereoselective Mannich-type reactions of ketones with Î±-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this