Diallyl cuprate

Undeca-l,2-diene treated sequentially with equimolecular quantities of -butyl-lithium and -propyl iodide in tetrahydrofuran -> tetradeca-4,5-diene. Y 96% purity 95%. F. e., also synthesis of allenes from bromoallenes, s. G. Linstrumelle and D. Midielot, Chem. Commun. 1975, 561 alkylation of allenes via Li-diallyl-cuprates cf. Tetrah. Let. 1976, 275. 

Scheme 4). cw-Cyclopentene-3,5-diol (25) is first converted into epoxide (26), which is then treated with lithium diallyl cuprate to yield the trans-oWyX alcohol (27). Tosylation of (27), followed by ozonolysis of the resulting tosylate and acetalization then produced (28). Hydrogenolysis of (28) produced (29), which was then smoothly converted into the key epoxide intermediate (30) by treatment with base. Reaction of the trimethylsilyl ether... 

Related 1,2-additions to imines in the -lactam area employing organocuprates have also met with considerable success. Net substitution reactions, proceeding via intermediate imino derivatives, have been achieved with lithium diallyl- and dialkyl-cuprates on educts such as (105) and (106). When a stereochemical label is present as in (107) and (108), the major products reflect trans addition to imines (109) and (110), respectively (Scheme 18). 

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