Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

Literature DB >> 20662502

Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

Uttam K Tambar¹, Sharon K Lee, James L Leighton.

Abstract

Enantioselective (formal) aza-Diels-Alder reactions between acylhydrazones and non-Danishefsky-type dienes have been developed. The reactions are promoted by a simple and economical chiral silicon Lewis acid and are typically conducted at ambient temperature. Both glyoxylate- and aliphatic aldehyde-derived hydrazones may be employed, as may variously substituted dienes, leading to the synthesis of a diverse array of tetrahydropyridines with good to excellent levels of enantioselectivity.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20662502 PMCID： PMC2918383 DOI： 10.1021/ja104480g

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

17 in total

1. Catalytic enantioselective aza-Diels-alder reactions of imines--an approach to optically active nonproteinogenic alpha-amino acids

Authors:
Journal: Chemistry Date: 2000-07-03 Impact factor: 5.236

2. Cooperative coexistence: effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines.

Authors: Magnus Rueping; Cengiz Azap
Journal: Angew Chem Int Ed Engl Date: 2006-11-27 Impact factor: 15.336

3. Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines.

Authors: Junji Itoh; Kohei Fuchibe; Takahiko Akiyama
Journal: Angew Chem Int Ed Engl Date: 2006-07-17 Impact factor: 15.336

4. Regulation of orthogonal functions in a dual catalyst system. Subservient role of a nonchiral Lewis acid in an asymmetric catalytic heteroatom Diels-Alder reaction.

Authors: Cory A Newman; Jon C Antilla; Pei Chen; Alexander V Predeus; Lee Fielding; William D Wulff
Journal: J Am Chem Soc Date: 2007-05-16 Impact factor: 15.419

5. Efficient and practical Ag-catalyzed cycloadditions between arylimines and the Danishefsky diene.

Authors: Nathan S Josephsohn; Marc L Snapper; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2003-04-09 Impact factor: 15.419

6. Origins of the regioselectivities in the Diels-Alder reactions of vinylindenes with 1,4-quinone monoketal and acrolein dienophiles.

Authors: Amy E Hayden; Jason DeChancie; Alexander H George; Mingji Dai; Maolin Yu; Samuel J Danishefsky; K N Houk
Journal: J Org Chem Date: 2009-09-04 Impact factor: 4.354

7. Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Brønsted acids.

Authors: Hua Liu; Lin-Feng Cun; Ai-Qiao Mi; Yao-Zhong Jiang; Liu-Zhu Gong
Journal: Org Lett Date: 2006-12-21 Impact factor: 6.005

8. Chiral copper complexes of phosphino sulfenyl ferrocenes as efficient catalysts for enantioselective formal Aza Diels-Alder reactions of N-sulfonyl imines.

Authors: Olga García Mancheño; Ramón Gómez Arrayás; Juan C Carretero
Journal: J Am Chem Soc Date: 2004-01-21 Impact factor: 15.419

Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

1. Catalytic enantioselective aza-Diels-alder reactions of imines--an approach to optically active nonproteinogenic alpha-amino acids

2. Cooperative coexistence: effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines.

3. Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines.

4. Regulation of orthogonal functions in a dual catalyst system. Subservient role of a nonchiral Lewis acid in an asymmetric catalytic heteroatom Diels-Alder reaction.

5. Efficient and practical Ag-catalyzed cycloadditions between arylimines and the Danishefsky diene.

6. Origins of the regioselectivities in the Diels-Alder reactions of vinylindenes with 1,4-quinone monoketal and acrolein dienophiles.

7. Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Brønsted acids.

8. Chiral copper complexes of phosphino sulfenyl ferrocenes as efficient catalysts for enantioselective formal Aza Diels-Alder reactions of N-sulfonyl imines.

9. Trifluoroacetyl-activated nitrogen-nitrogen bond cleavage of hydrazines by samarium(II) iodide.

10. A direct route to fluostatin C by a fascinating Diels-Alder reaction.

1. Recent advances in the application of ring-closing metathesis for the synthesis of unsaturated nitrogen heterocycles.

2. Highly enantioselective Mannich reactions with α-aryl silyl ketene acetals and imines.

3. A single step approach to piperidines via Ni-catalyzed β-carbon elimination.