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Literature DB >> 16597111

De novo chiral amino alcohols in catalyzing asymmetric additions to aryl aldehydes.

Jian Huang¹, James C Ianni, Jennifer E Antoline, Richard P Hsung, Marisa C Kozlowski.

Abstract

[reaction: see text] A de novo structural class of chiral amino alcohol catalysts has been identified through a synergistic effort combining novel architectures from [4 + 3] cycloadditions and quantum mechanical interaction field predictions that closely match subsequent experimental measurements.

Entities: Chemical

Mesh：

Substances：
Aldehydes
Amino Alcohols

Year: 2006 PMID： 16597111 DOI： 10.1021/ol0600640

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

Authors: Zhenlei Song; Richard P Hsung; Ting Lu; Andrew G Lohse
Journal: J Org Chem Date: 2007-11-03 Impact factor: 4.354

2. Quantum Molecular Interaction Field Models of Substrate Enantioselection in Asymmetric Processes.

Authors: Marisa C Kozlowski; James C Ianni
Journal: J Mol Catal A Chem Date: 2010-06-01

3. A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Application of quantitative structure activity/selectivity relationships.

Authors: Scott E Denmark; Nathan D Gould; Larry M Wolf
Journal: J Org Chem Date: 2011-05-06 Impact factor: 4.354

De novo chiral amino alcohols in catalyzing asymmetric additions to aryl aldehydes.

1. Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

2. Quantum Molecular Interaction Field Models of Substrate Enantioselection in Asymmetric Processes.

3. A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Application of quantitative structure activity/selectivity relationships.

4. (4+3) cycloaddition reactions of nitrogen-stabilized oxyallyl cations.

5. Saucy-Marbet Rearrangements of Alkynyl Halides in the Synthesis of Highly Enantiomerically Enriched Allenyl Halides.

6. Synthesis of amido-spiro[2.2]pentanes via Simmons-Smith cyclopropanation of allenamides.

Review 7. Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.