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Pure Appl. Chem., 2009, Vol. 81, No. 2, pp. 235-246

1-Lithio-1,3-dienes as useful building blocks in organic synthesis

Wen-Xiong Zhang and Zhenfeng Xi

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China

Abstract: Both intermolecular reactivities toward C-O and C-N unsaturated substrates and intramolecular reactions of various 1-lithio-1,3-dienes are briefly summarized. Results reveal that intramolecular synergy between the alkenyllithium moiety and the butadienyl skeleton make 1-lithio-1,3-diene derivatives useful and unique as building blocks in organic synthesis. It is demonstrated that substitution patterns and the nature of the substituents on the butadienyl skeleton have remarkable effects on reaction pathways.