Literature DB >> 12201714

Highly enantioselective reformatsky reaction of ketones: chelation-assisted enantioface discrimination.

Akio Ojida1, Toru Yamano, Naohiro Taya, Akihiro Tasaka.   

Abstract

[reaction: see text] Highly enantioselective Reformatsky reaction of ketones was accomplished using cinchona alkaloids as chiral ligands. Chelation with the sp(2)-nitrogen adjacent to the reactive carbonyl center contributed the enantioface discrimination for the high enantioselectivities.

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Year:  2002        PMID: 12201714     DOI: 10.1021/ol0263189

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


  5 in total

1.  Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

Authors:  Evan H Tallmadge; David B Collum
Journal:  J Am Chem Soc       Date:  2015-10-05       Impact factor: 15.419

2.  Preclinical assessment of Orteronel(®), a CYP17A1 enzyme inhibitor in rats.

Authors:  Mohd Zainuddin; A B Vinod; Sandip Dhondiram Gurav; Anitha Police; Avinash Kumar; Chandan Mithra; Purushottam Dewang; Raghava Reddy Kethiri; Ramesh Mullangi
Journal:  Eur J Drug Metab Pharmacokinet       Date:  2014-10-09       Impact factor: 2.441

3.  Lithium Amino Alkoxide-Evans Enolate Mixed Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol.

Authors:  Janis Jermaks; Evan H Tallmadge; Ivan Keresztes; David B Collum
Journal:  J Am Chem Soc       Date:  2018-02-19       Impact factor: 15.419

4.  Structure-Reactivity Relationships in Lithiated Evans Enolates: Influence of Aggregation and Solvation on the Stereochemistry and Mechanism of Aldol Additions.

Authors:  Evan H Tallmadge; Janis Jermaks; David B Collum
Journal:  J Am Chem Soc       Date:  2015-12-24       Impact factor: 15.419

5.  Synthetic, Mechanistic, and Biological Interrogation of Ginkgo biloba Chemical Space En Route to (-)-Bilobalide.

Authors:  Robert M Demoret; Meghan A Baker; Masaki Ohtawa; Shuming Chen; Ching Ching Lam; Sophia Khom; Marisa Roberto; Stefano Forli; Kendall N Houk; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419

  5 in total

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