High chelation control of three contiguous stereogenic centers in the Reformatsky reactions of indium enolates with alpha-hydroxy ketones: unexpected stereochemistry of lactone formation |
| |
| Authors: | Babu Srinivasarao Arulananda Yasuda Makoto Okabe Yuji Shibata Ikuya Baba Akio |
| |
| Affiliation: | Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Japan. |
| |
| Abstract: | [reaction: see text] A boat-type of chelated bicyclic transition state involving highly diastereoselective construction of three contiguous stereogenic centers in the Reformatsky reaction of indium enolates with alpha-alkoxy/hydroxy ketones is proposed. alpha-Hydroxy ketones with indium enolates furnished highly diastereoselective lactones, while alpha-alkoxy ketones gave acyclic esters in moderate selectivities. X-ray structure analyses of key products unequivocally revealed the unexpected stereochemistry of products and the reaction pathway. |
| |
| Keywords: | |
| 本文献已被 PubMed 等数据库收录！ |
