Cyclopropene Derivatives as Precursors to Enantioenriched Cyclopropanols and n-Butenals Possessing Quaternary Carbon Stereocenters†
Marwan Simaan
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
Search for more papers by this authorDr. Pierre-Olivier Delaye
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
Search for more papers by this authorProf. Dr. Min Shi
State Key Laboratory of Organometallic Chemistry. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Lu, Shanghai, 200032 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ilan Marek
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)Search for more papers by this authorMarwan Simaan
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
Search for more papers by this authorDr. Pierre-Olivier Delaye
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
Search for more papers by this authorProf. Dr. Min Shi
State Key Laboratory of Organometallic Chemistry. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Lu, Shanghai, 200032 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ilan Marek
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)Search for more papers by this authorThis research was supported by the Israel Science Foundation and the National Natural Science Foundation of China joint research program (grant No. 316/13). I.M. is holder of the Sir Michael and Lady Sobell Academic Chair.
Abstract
The diastereoselective carbocupration reaction of cyclopropenylmethyl ethers followed by addition of oxenoid leads to the formation of diastereo- and enantiomerically enriched 2,2,3,3-tetrasubstituted cyclopropanol derivatives. Ring fragmentation of the copper cyclopropanolate leads to acyclic butenal derivatives possessing enantiomerically enriched α-quaternary carbon stereocenters in a single-pot operation.
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