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Origin of stereochemistry in Meyers enolate alkylations. Importance of major enolate structure and population in tetrahydrofuran

✍ Scribed by Yasuhiro Ikuta; Shuji Tomoda

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 167 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01223-1

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✦ Synopsis

It was found that in tetrahydrofuran solution, predominance (99.2%) of the highly stabilized Meyers enolate (1,5-dimethylpyrrolidin-2-one lithium enolate (1)) isomer with intramolecular Li-p C C coordination from the endo-face (Ct-endo) may be responsible for exceedingly high endo-selectivity in Meyers enolate alkylation.

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