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Literature DB >> 15067138

O-nitroso aldol synthesis: Catalytic enantioselective route to alpha-aminooxy carbonyl compounds via enamine intermediate.

Norie Momiyama¹, Hiromi Torii, Susumu Saito, Hisashi Yamamoto.

Abstract

The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Brønsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.

Entities: Chemical

Mesh：

Substances：

Year: 2004 PMID： 15067138 PMCID： PMC397388 DOI： 10.1073/pnas.0307785101

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

22 in total

1. The first direct and enantioselective cross-aldol reaction of aldehydes.

Authors: Alan B Northrup; David W C MacMillan
Journal: J Am Chem Soc Date: 2002-06-19 Impact factor: 15.419

2. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.

Authors: Linh Hoang; S Bahmanyar; K N Houk; Benjamin List
Journal: J Am Chem Soc Date: 2003-01-08 Impact factor: 15.419

3. Direct catalytic asymmetric aldol reactions of aldehydes.

Authors: Anders Bøgevig; Nagaswamy Kumaragurubaran; Karl Anker Jørgensen
Journal: Chem Commun (Camb) Date: 2002-03-21 Impact factor: 6.222

4. 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

5. 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

6. Simple synthesis of alpha-hydroxyamino carbonyl compounds: new scope of the nitroso aldol reaction.

Authors: Norie Momiyama; Hisashi Yamamoto
Journal: Org Lett Date: 2002-10-17 Impact factor: 6.005

7. The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles.

Authors: Wolfgang Notz; Fujie Tanaka; Shin-Ichi Watanabe; Naidu S Chowdari; James M Turner; Rajeswari Thayumanavan; Carlos F Barbas
Journal: J Org Chem Date: 2003-12-12 Impact factor: 4.354

8. Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines.

Authors: Paolo Melchiorre; Karl Anker Jørgensen
Journal: J Org Chem Date: 2003-05-30 Impact factor: 4.354

9. Rapid fluorescent screening for bifunctional amine-acid catalysts: efficient syntheses of quaternary carbon-containing aldols under organocatalysis.

Authors: Nobuyuki Mase; Fujie Tanaka; Carlos F Barbas
Journal: Org Lett Date: 2003-11-13 Impact factor: 6.005

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

9 in total

1. Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis.

Authors: Norie Momiyama; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2005-02-02 Impact factor: 15.419

2. Proline Sulfonamide-Based Organocatalysis: Better Late than Never.

Authors: Hua Yang; Rich G Carter
Journal: Synlett Date: 2010-09-01 Impact factor: 2.454

3. NHC-catalyzed reactions of aryloxyacetaldehydes: a domino elimination/conjugate addition/acylation process for the synthesis of substituted coumarins.

Authors: Eric M Phillips; Manabu Wadamoto; Howard S Roth; Andrew W Ott; Karl A Scheidt
Journal: Org Lett Date: 2009-01-01 Impact factor: 6.005

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

Authors: Peng Jiao; Masanori Kawasaki; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

5. Regiochemical Reversals in Nitrosobenzene Reactions with Carbonyl Compounds: α-Aminooxyketone versus α-Hydroxyaminoketone Products.

Authors: Donna J Nelson; Ravi Kumar
Journal: European J Org Chem Date: 2012-10