A Remarkable Effect of a 3-OLi Group to Fix the Conformation of Lithium 1-Phenyl-1-propanides

Tatsuya Kato; Shinji Marumoto; Toshio Sato; Isao Kuwajima

doi:10.1055/s-1990-21205

Synlett 1990; 1990(11): 671-672
DOI: 10.1055/s-1990-21205

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A Remarkable Effect of a 3-OLi Group to Fix the Conformation of Lithium 1-Phenyl-1-propanides

Tatsuya Kato^* , Shinji Marumoto, Toshio Sato, Isao Kuwajima

^*Department of Chemistry, Tokyo Institute of Technology, Meguro, Tokyo 152, Japan

Abstract

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Dilithium 2-butyl-3-oxido-1-phenyl-1-propanide (PhCH(Li)CH(Bu)CH₂OLi) was generated by treating (E)- or (Z)-cinnamyl alcohol with ca. 2 equivalents of butyllithium, and the stereochemical outcome was examined by reaction with several electrophiles: The reaction took place in a highly syn-selective fashion, and preferential formation of a benzylic lithium species having sp²-like character has been suggested.

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