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 A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.

Literature DB >> 19343748

A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.

Peng Jiao¹, Masanori Kawasaki, Hisashi Yamamoto.

Abstract

Chiral 1,2-diols have been prepared from alpha-aminoxylated aldehydes or cyclohexanone and Grignard reagents with L-proline or its tetrazole derivative as the catalyst. The presence of the ate complex of CeCl(3)2 LiCl is essential for the high overall yields and good selectivities (see scheme; DMSO = dimethyl sulfoxide, THF = tetrahydrofuran, Tol = tolyl).

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2009 PMID： 19343748 PMCID： PMC3443970 DOI： 10.1002/anie.200900682

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

16 in total

1. A facile and rapid route to highly enantiopure 1,2-diols by novel catalytic asymmetric alpha-aminoxylation of aldehydes.

Authors: Guofu Zhong
Journal: Angew Chem Int Ed Engl Date: 2003-09-15 Impact factor: 15.336

2. Concise total synthesis and structure assignment of TAN-1085.

Authors: Ken Ohmori; Keiji Mori; Yuji Ishikawa; Hideyuki Tsuruta; Shunsuke Kuwahara; Nobuyuki Harada; Keisuke Suzuki
Journal: Angew Chem Int Ed Engl Date: 2004-06-14 Impact factor: 15.336

3. Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones.

Authors: Yujiro Hayashi; Junichiro Yamaguchi; Tatsunobu Sumiya; Kazuhiro Hibino; Mitsuru Shoji
Journal: J Org Chem Date: 2004-09-03 Impact factor: 4.354

4. Direct proline-catalyzed asymmetric alpha-aminoxylation of ketones.

Authors: Yujiro Hayashi; Junichiro Yamaguchi; Tatsunobu Sumiya; Mitsuru Shoji
Journal: Angew Chem Int Ed Engl Date: 2004-02-20 Impact factor: 15.336

Review 5. Recent advances in catalytic, enantioselective alpha aminations and alpha oxygenations of carbonyl compounds.

Authors: Jacob M Janey
Journal: Angew Chem Int Ed Engl Date: 2005-07-11 Impact factor: 15.336

6. Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum.

Authors: Allan U Barlan; Arindrajit Basak; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2006-09-04 Impact factor: 15.336

7. Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Authors: Yian Shi
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

8. The crystallographic structure of a Lewis acid-assisted chiral Brønsted acid as an enantioselective protonation reagent for silyl enol ethers.

Authors: Kazuaki Ishihara; Daisuke Nakashima; Yukihiro Hiraiwa; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2003-01-08 Impact factor: 15.419

9. Organocatalyzed asymmetric alpha-aminoxylation of aldehydes and ketones--an efficient access to enantiomerically pure alpha-hydroxycarbonyl compounds, diols, and even amino alcohols.

Authors: Pedro Merino; Tomas Tejero
Journal: Angew Chem Int Ed Engl Date: 2004-06-07 Impact factor: 15.336

10. The direct and enantioselective organocatalytic alpha-oxidation of aldehydes.

Authors: Sean P Brown; Michael P Brochu; Christopher J Sinz; David W C MacMillan
Journal: J Am Chem Soc Date: 2003-09-10 Impact factor: 15.419

7 in total

1. Simple strategy for synthesis of optically active allylic alcohols and amines by using enantioselective organocatalysis.

Authors: Hao Jiang; Nicole Holub; Karl Anker Jørgensen
Journal: Proc Natl Acad Sci U S A Date: 2010-06-14 Impact factor: 11.205

A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.

1. A facile and rapid route to highly enantiopure 1,2-diols by novel catalytic asymmetric alpha-aminoxylation of aldehydes.

2. Concise total synthesis and structure assignment of TAN-1085.

3. Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones.

4. Direct proline-catalyzed asymmetric alpha-aminoxylation of ketones.

Review 5. Recent advances in catalytic, enantioselective alpha aminations and alpha oxygenations of carbonyl compounds.

6. Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum.

7. Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

8. The crystallographic structure of a Lewis acid-assisted chiral Brønsted acid as an enantioselective protonation reagent for silyl enol ethers.

9. Organocatalyzed asymmetric alpha-aminoxylation of aldehydes and ketones--an efficient access to enantiomerically pure alpha-hydroxycarbonyl compounds, diols, and even amino alcohols.

10. The direct and enantioselective organocatalytic alpha-oxidation of aldehydes.

1. Simple strategy for synthesis of optically active allylic alcohols and amines by using enantioselective organocatalysis.

2. An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

3. Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

4. Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline.

5. Enantioselective total synthesis of (R)-(-)-complanine.

6. Palladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds.

7. Reaction of selected carbohydrate aldehydes with benzylmagnesium halides: benzyl versus o-tolyl rearrangement.